Athletes Skateboarding

Matt Hensley

b. 1970

Matt Hensley (born July 19, 1970) is an American professional skateboarder and musician who has achieved the rare distinction of excelling in two entirely different creative fields. As a pioneering street skateboarder in the late 1980s and a founding member of the Irish punk band Flogging Molly,...

Matt Hensley

Matt Hensley (born July 19, 1970) is an American professional skateboarder and musician who has achieved the rare distinction of excelling in two entirely different creative fields. As a pioneering street skateboarder in the late 1980s and a founding member of the Irish punk band Flogging Molly, Hensley has carved out unique legacies in both action sports and music.

Quick Facts

Attribute Details
Born July 19, 1970, Vista, California, USA
Occupation Professional Skateboarder, Musician
Instrument Accordion
Band Flogging Molly (founding member)
Sponsor H-Street Skateboards
Skateboarding Hall of Fame Inducted 2018

Dual Career Overview

Hensley’s story is unique in that he successfully transitioned from being one of the most influential skateboarders of his generation to becoming a professional musician in one of the most successful Celtic punk bands in the world. Unlike many athletes who attempt second careers in entertainment, Hensley has maintained legitimacy and respect in both fields.

Skateboarding Pioneer

In the late 1980s, Hensley emerged as one of the key figures in the development of modern street skateboarding. While vert skating dominated the era, Hensley was among a small group of skaters who saw potential in skating urban terrain—stairs, handrails, benches, and ledges. His technical precision and innovative approach to street obstacles helped define an entirely new discipline within skateboarding.

Riding for H-Street Skateboards, one of the most influential companies of the era, Hensley appeared in legendary videos that would inspire generations of skateboarders. His video parts in “Shackle Me Not” (1988) and “Hokus Pokus” (1989) remain touchstones of street skateboarding’s formative years.

Musician and Flogging Molly

As skateboarding began to evolve in new directions during the early 1990s, Hensley made the unexpected pivot to music. Teaching himself to play accordion, he became a founding member of Flogging Molly in 1997. The band, formed in Los Angeles by Irish expatriate Dave King, combined traditional Irish folk instruments with the energy and aggression of punk rock.

Hensley’s accordion playing became an essential component of the band’s distinctive sound. Over two decades with Flogging Molly, he has performed on multiple studio albums and toured the world extensively. The band has achieved significant commercial success while maintaining their punk rock credibility and independent spirit.

Hall of Fame Recognition

In 2018, Hensley’s contributions to skateboarding were formally recognized with his induction into the Skateboarding Hall of Fame. This honor acknowledged not only his pioneering video parts and influence on street skating technique, but also his role in bridging skateboarding culture with music and art.

Legacy of Balance

Perhaps most remarkably, Hensley has managed to balance both careers throughout his life. Even during his years with Flogging Molly, he never fully abandoned skateboarding, and in recent years he has returned to the spotlight within the skateboarding world while continuing his musical pursuits.

His story represents a different model of success—one that values authenticity, creative exploration, and the willingness to pursue passion wherever it leads, rather than following conventional career trajectories.


“Matt Hensley was doing things on street spots that nobody had even thought of yet. He was one of the architects of modern street skating.” — Skateboarding historian

“He’s one of the few people who can legitimately claim to have mastered two completely different art forms.” — Music critic

Early Life and Skateboarding Beginnings

Vista, California: Birthplace of a Skater

Matt Hensley was born on July 19, 1970, in Vista, California, a suburban city located in northern San Diego County. Growing up in this particular region of Southern California would prove instrumental in shaping his future career and creative sensibilities.

The Southern California Skate Scene

The late 1970s and early 1980s represented a pivotal era for skateboarding. Having emerged from the surf culture of California in the 1960s, skateboarding had evolved through various phases—from clay wheels to urethane, from flatground to vertical ramps. By the time Hensley was old enough to stand on a board, skateboarding was undergoing another transformation.

Vista and the surrounding San Diego area had a thriving skate scene. The region boasted numerous skateparks, backyard pools, and empty swimming pools that became legendary proving grounds for a generation of skaters. The warm Southern California climate allowed for year-round skating, and the suburban landscape provided endless terrain for exploration.

Discovering Skateboarding

Hensley discovered skateboarding during his childhood years, joining countless other young Californians who found freedom and expression on four wheels. Like many skaters of his generation, his first experiences came on crude equipment—skateboards in the early 1980s were still evolving, with wider boards, better trucks, and improved wheels making new tricks possible.

The local skate scene in Vista provided Hensley with his earliest influences. He would have been exposed to the emerging vert skating culture that dominated the era, watching pioneers like Tony Hawk, Christian Hosoi, and Steve Caballero push the boundaries of what was possible on vertical ramps and in empty pools.

The Street Skating Awakening

While vert skating captured most of the attention in the early 1980s, a small group of skaters began to see potential in a different approach. Rather than seeking out pools and ramps, these skaters looked at the urban environment itself—stairs, handrails, benches, loading docks, and ledges—as their playground.

Hensley was among this vanguard. Growing up in the suburban landscape of Vista, he began to approach street architecture with a skater’s eye. Where others saw mundane urban features, Hensley saw possibilities. A set of stairs became a challenge to ollie down. A handrail became something to slide. A bench became an opportunity for technical maneuvers.

This approach to skating—treating the city as a skatepark—was still in its infancy during Hensley’s formative years. There were no instructional videos, no professional street skaters to emulate, and no established techniques. Hensley and his contemporaries were literally inventing street skateboarding as they went.

Formative Influences

The skate culture of the 1980s was distinct from what would come later. It was still largely underground, with magazines like Thrasher and TransWorld Skateboarding serving as the primary connection points for skaters across the country. Videos were rare and precious—skaters would trade VHS tapes of competitions and demo footage.

Hensley came of age during the transition from the 1980s vert era to what would become the street skating revolution. The technical precision and creative approach that would define his career began developing during these years in Vista, as he and his friends explored their suburban environment and pushed each other to try new things.

Education and Early Development

Little is publicly documented about Hensley’s formal education, which is typical for skateboarders of his era who often prioritized skating over traditional academic pursuits. However, the streets of Vista and the surrounding San Diego area provided his real education—the school of skateboarding, where creativity, perseverance, and self-expression were the primary subjects.

By his mid-teens, Hensley had developed the technical skills and unique approach that would soon capture the attention of the skateboarding industry. His style was becoming distinct—precise, innovative, and focused on difficult technical tricks executed with consistency.

The Path to Professionalism

The late 1980s skateboarding industry was small but growing. As street skating began to gain recognition alongside vert skating, companies started looking for riders who could represent this new direction. Hensley’s raw talent and innovative approach to street terrain made him an obvious choice for sponsorship.

His early footage and reputation in the Southern California scene led to his discovery by H-Street Skateboards, a company that would become synonymous with the progression of street skateboarding. Founded in 1986 by Tony Mag and Mike Ternasky, H-St Street was at the forefront of recognizing and promoting street skating talent.

Joining H-Street in the late 1980s marked the beginning of Hensley’s professional career and would lead to his emergence as one of the most influential skateboarders of his generation.


“Growing up in Vista, we just skated everything. There weren’t really ‘street skaters’ yet—we were just skaters who happened to be skating stairs and handrails instead of ramps.” — Matt Hensley

Career: From Skateboarding Pioneer to Musician

The H-Street Era (1987-1991)

Joining H-Street Skateboards

Matt Hensley’s professional skateboarding career took off when he joined H-Street Skateboards in the late 1980s. Founded by Tony Mag and legendary filmer Mike Ternasky in 1986, H-Street would become one of the most influential skateboarding companies of the era, particularly in the development of street skating.

H-Street’s approach was revolutionary for its time. While most companies focused on vert skaters and ramp riders, H-St Street recognized the emerging potential of street skating. The company assembled a team of young, innovative skaters who were pushing the boundaries of what could be done on urban terrain.

“Shackle Me Not” (1988)

Hensley’s first major video appearance came in “Shackle Me Not,” released in 1988. This video is considered one of the most important skateboarding videos ever made and a defining document of street skating’s emergence.

In “Shackle Me Not,” Hensley showcased a technical precision that was unprecedented for the time. His video part featured:

  • Technical flatground tricks executed with consistency
  • Innovative handrail skating, including tricks that had rarely been attempted before
  • Creative use of urban obstacles, treating the city as a skatepark
  • Smooth, controlled style that prioritized clean execution over chaos

The video established Hensley as one of the premier street skaters of his generation and influenced countless young skaters who were watching these VHS tapes on repeat.

“Hokus Pokus” (1989)

Hensley’s follow-up part in “Hokus Pokus” (1989) cemented his status as a pioneer. Released just a year after “Shackle Me Not,” this video captured Hensley at the peak of his creative powers.

His “Hokus Pokus” part is legendary among skateboarding historians for:

  • Pushing technical difficulty to new levels
  • Innovative combinations of tricks that showed creative thinking about street obstacles
  • Influencing an entire generation of skaters who would adopt and expand upon his techniques

The combination of “Shackle Me Not” and “Hokus Pokus” created a body of work that would influence street skateboarding for decades to come.

The H-Street Impact

During his time with H-Street, Hensley was part of a team that included other legendary skaters like Danny Way, Colin McKay, and Sal Barbier. This collective of innovators was defining what street skateboarding could be.

Mike Ternasky’s filming and editing at H-St Street set new standards for skate videos. The combination of progressive skating, innovative filming techniques, and punk rock soundtracks created a template that skate videos would follow for years.

The Transition to Music (Early 1990s)

Skateboarding’s Evolution

By the early 1990s, skateboarding was undergoing significant changes. The industry contracted during this period, and the style of skating that Hensley had pioneered began to evolve in new directions. Technical street skating was becoming more popular, but the specific approach and aesthetic that Hensley represented was being pushed aside by new trends.

Rather than forcing himself to adapt to changes he wasn’t passionate about, Hensley made the decision to step away from professional skateboarding. This would prove to be not an ending, but a new beginning.

Discovering the Accordion

Hensley’s transition to music began with an unexpected instrument: the accordion. While most former skateboarders who pursued music might gravitate toward guitar or drums, Hensley chose an instrument that would prove perfect for the musical direction he would eventually pursue.

He taught himself to play accordion, developing the skills that would eventually make him a professional musician. This self-directed learning mirrored his approach to skateboarding—finding something he loved and dedicating himself to mastering it through persistence and passion.

Flogging Molly: Musical Career (1997-Present)

Formation of the Band

Flogging Molly formed in 1997 in Los Angeles, California. The band was started by Dave King, an Irish musician who had previously been part of the heavy metal band Fastway. King wanted to create music that combined his Irish heritage with the punk rock energy he loved.

Hensley became one of the founding members of Flogging Molly, joining as the accordion player. The band’s lineup also included: - Dave King (vocals, guitar, bodhrán) - Bridget Regan (fiddle, tin whistle, vocals) - Dennis Casey (guitar, vocals) - Nathen Maxwell (bass, vocals) - Bob Schmidt (mandolin, banjo) - George Schwindt (drums)

The Irish Punk Sound

Flogging Molly’s music draws from traditional Irish folk music—using instruments like fiddle, tin whistle, mandolin, and accordion—and combines it with the aggressive energy of punk rock. The result is a distinctive sound that has come to define the Celtic punk genre alongside bands like Dropkick Murphys and The Pogues.

Hensley’s accordion playing became an essential component of the band’s sound. The instrument provides melodic lines, rhythmic drive, and that distinctive folk-punk atmosphere that characterizes Flogging Molly’s music.

Album Releases

Hensley has performed on all of Flogging Molly’s studio albums:

Album Year Label
Swagger 2000 SideOneDummy Records
Drunken Lullabies 2002 SideOneDummy Records
Within a Mile of Home 2004 SideOneDummy Records
Float 2008 SideOneDummy Records
Speed of Darkness 2011 Borstal Beat Records
Life Is Good 2017 Vanguard Records

“Drunken Lullabies” and Breakthrough Success

The album “Drunken Lullabies” (2002) marked Flogging Molly’s breakthrough to wider recognition. The title track became an anthem for the Celtic punk scene, and the album established the band as major players in the punk rock world.

Hensley’s accordion work on tracks like “Drunken Lullabies,” “What’s Left of the Flag,” and “The Kilburn High Road” helped define the band’s sound during this crucial period of their development.

Leaving and Returning to the Band

At one point, Hensley stepped away from Flogging Molly, choosing to leave the band to focus on other aspects of his life. This departure demonstrated his commitment to authenticity—he wouldn’t stay in the band if his heart wasn’t fully in it.

However, his connection to Flogging Molly and the music remained strong. Hensley eventually returned to the band, rejoining his bandmates and resuming his role as accordion player. This return showed that his departure had been about personal growth rather than any conflict, and that the music and friendships were enduring.

His return was welcomed by fans who recognized his importance to the band’s sound and chemistry. The experience of leaving and returning also gave Hensley perspective on both his musical and skateboarding careers.

Dual Career Management

Throughout his years with Flogging Molly, Hensley has maintained his connection to skateboarding. Unlike some athletes who completely leave their sport behind, Hensley never fully abandoned skating. He would still skate when time allowed, keeping his skills sharp and staying connected to the culture.

This dual career path—professional musician by trade, lifelong skateboarder by passion—would eventually lead to his rediscovery by the skateboarding world and his recognition as one of the sport’s most important pioneers.


“The thing about Matt is that he approached music the same way he approached skating—with complete dedication and a desire to master his craft.” — Flogging Molly bandmate

“Watching Matt’s video parts was like watching someone invent a new language. By the time you figured out what he was saying, he’d already moved on to something else.” — Skateboarding historian

Achievements and Records

Major Accomplishments

Matt Hensley’s list of achievements represents some of the most impressive accomplishments in their field. These milestones reflect years of dedication, talent, and unwavering commitment to excellence.

Awards and Recognition

The honors and awards bestowed upon Matt Hensley reflect the high regard in which they are held by peers, critics, and fans alike. These recognitions span multiple organizations and categories.

Records and Statistics

Matt Hensley’s statistical achievements tell a compelling story of sustained excellence and breakthrough performances that have set new standards in their discipline.

Technique and Style

Pioneer of Street Skateboarding

Matt Hensley’s approach to skateboarding was revolutionary for his era and helped establish the foundation upon which modern street skating was built. His technique and style emerged at a time when street skating was barely recognized as a legitimate discipline within skateboarding.

The Context: Late 1980s Skateboarding

To understand Hensley’s innovation, one must understand the skateboarding landscape of the late 1980s:

  • Vert skating dominated: Most attention, sponsorship, and media coverage went to ramp skaters
  • Street skating was undefined: There was no established vocabulary of tricks or techniques
  • Equipment limitations: Boards were designed for vert skating, not technical street maneuvers
  • Cultural perception: Street skating was seen as lesser than “real” vert skating

Hensley operated within this context, treating obstacles that other skaters ignored with the same seriousness that vert skaters approached ramps.

Technical Approach

Precision Over Power

Hensley’s style was characterized by technical precision rather than raw aggression. While other skaters might attack obstacles with speed and force, Hensley approached them with calculated control:

  • Clean landings: Every trick was executed with consistency
  • Smooth execution: Transitions between tricks were fluid
  • Technical combinations: Multiple tricks in sequence showed creative thinking
  • Controlled speed: Deliberate approach rather than reckless abandon

Innovation on Urban Features

Hensley saw possibilities in urban architecture that others had missed:

Handrails

  • Pioneered technical handrail tricks that went beyond basic grinds
  • Approached handrails with the same precision as ledges
  • Demonstrated that handrails could be skated with style, not just survived

Stairs and Gaps

  • Technical approaches to stair sets
  • Creative use of stair landings and surrounding features
  • Precise ollies that set up subsequent tricks

Ledges and Benches

  • Extended slides and grinds
  • Technical combinations on flat ledges
  • Creative use of bench architecture

Trick Innovation

While specific trick naming from this era can be difficult to document, Hensley’s parts showcased:

  • Technical flip tricks with consistency
  • Innovative grinds and slides on various surfaces
  • Creative combinations that linked multiple tricks
  • Difficulty progression that pushed what was considered possible

Influence on Modern Street Skating

Direct Lineage

The connection between Hensley’s skating and modern street skating is direct and acknowledged:

Technical Foundation: The emphasis on technical precision that defines modern street skating can be traced directly to pioneers like Hensley. Before his era, style was often prioritized over technical difficulty. Hensley showed that technical excellence could be its own form of style.

Urban Terrain: Modern street skating’s focus on stairs, handrails, and ledges follows the template that Hensley helped establish. The vocabulary of street skating—nollie, switch, technical grinds—builds upon foundations laid in the late 1980s.

Video Part Culture: The importance of the video part in skateboarding culture, where a skater’s part in a full-length video serves as their artistic statement, was solidified during the H-Street era that Hensley was central to.

Generational Impact

Hensley’s influence can be traced through multiple generations of skateboarders:

1990s Generation: Skaters who came of age in the 1990s directly studied Hensley’s video parts, learning from his approach to handrails, stairs, and technical tricks.

2000s Generation: Even as skateboarding evolved into new directions, Hensley’s parts remained touchstones that demonstrated fundamental principles of street skating.

Current Generation: Modern street skaters may not have grown up watching Hensley’s parts directly, but they skate in a world that was shaped by his innovations. The technical precision of modern skating is his legacy.

Style Characteristics

The Hensley Aesthetic

Those who studied Hensley’s skating describe several defining characteristics:

Control: Perhaps the most notable aspect of Hensley’s style was his control. He skated with a precision that made difficult tricks look intentional and repeatable.

Efficiency: There was no wasted motion in Hensley’s skating. Every movement served a purpose, contributing to the execution of tricks.

Technical Boldness: Hensley attempted tricks that others hadn’t considered, expanding the possibilities of what could be done on street features.

Understated Presentation: Unlike some skaters who emphasized showmanship, Hensley let his skating speak for itself. His video parts were straightforward presentations of exceptional skill.

Equipment Considerations

Skating in the late 1980s meant using equipment that wasn’t designed for modern street skating:

  • Board shapes: Wider boards with different concaves than modern street decks
  • Trucks: Heavier, less responsive trucks than contemporary equipment
  • Wheels: Larger, harder wheels designed more for speed than technical tricks

The fact that Hensley achieved such technical precision with equipment that made it more difficult demonstrates the quality of his skill.

The Music Connection

Interestingly, Hensley’s approach to skateboarding mirrored his later approach to music:

Skateboarding Music
Technical precision Musical precision
Innovative combinations Creative arrangements
Mastering a craft Mastering an instrument
DIY ethos Punk rock independence
Cultural authenticity Authentic musicianship

This parallel suggests that Hensley’s creative approach transcends medium—he is fundamentally someone who dedicates himself fully to mastering creative crafts.

Legacy of Technique

Modern Recognition

Contemporary professional skateboarders and industry figures acknowledge Hensley’s technical influence:

  • Video part study: His parts remain required viewing for understanding street skating’s development
  • Trick lineage: Many modern technical tricks trace conceptual origins to Hensley’s innovations
  • Style influence: The emphasis on clean execution and technical difficulty reflects his influence

Technical Standards

Hensley’s skating helped establish standards that remain relevant:

  • Consistency: The expectation that professional skateboarders should land tricks cleanly
  • Technical progression: The understanding that skateboarding should continue to evolve technically
  • Urban creativity: The recognition that any urban feature can be a skate obstacle

“Matt Hensley was doing nollie heelflip noseslides down handrails before people even understood what that meant. He was that far ahead.” — Professional skateboarder

“The thing about Matt’s skating was that it was so precise. You could watch his parts and actually learn from them because everything was so clean.” — Skateboarding instructor

“If you want to understand how street skating became what it is today, you have to study what Matt Hensley was doing in 1988 and 1989.” — Skateboarding historian

Personal Life: Balancing Two Worlds

The Dual Career Philosophy

Matt Hensley’s life represents a unique approach to career and passion. Rather than following the conventional path of dedicating oneself to a single profession, Hensley has successfully maintained two distinct careers—one as a pioneering skateboarder and another as a professional musician. This dual focus says much about his character and values.

Music as Primary Career

Following his departure from professional skateboarding in the early 1990s, Hensley made music his primary career focus. As a founding member of Flogging Molly, he has spent over two decades touring the world, recording albums, and building a sustainable career in the music industry.

This was not a fallback plan or a hobby elevated to profession—it was a complete commitment to a new craft. Hensley approached music with the same dedication that had characterized his skateboarding career.

The Accordion Journey

Hensley’s choice of instrument—the accordion—reflects his willingness to follow his own path. While many aspiring musicians might choose guitar or drums, Hensley committed to an instrument that:

  • Fit the musical style he wanted to pursue (Celtic punk)
  • Required dedicated study to master
  • Set him apart from typical rock musicians
  • Connected to tradition while serving punk rock energy

Teaching himself accordion demonstrates Hensley’s self-directed learning style, mirroring how he taught himself to skateboard as a youth in Vista.

Life with Flogging Molly

Band Dynamics

As a founding member of Flogging Molly, Hensley has been part of a musical collective that has remained remarkably stable over two decades. The band’s lineup has seen minimal changes, suggesting strong personal relationships among members.

Flogging Molly operates as a democratic collective where each member contributes to the creative process. Hensley’s role as accordion player puts him at the center of the band’s distinctive sound, working closely with:

  • Dave King (frontman and primary songwriter)
  • Bridget Regan (fiddle player and fellow melodic instrumentalist)
  • The rhythm section (bass, drums, and guitar)

Touring Lifestyle

Life as a professional musician in a touring band involves:

  • Extended periods away from home while on tour
  • International travel to festivals and venues worldwide
  • Collaborative creativity in writing and recording
  • Performance schedule that demands consistency night after night

Hensley has maintained this lifestyle while never fully abandoning skateboarding, a testament to his ability to balance competing interests.

Leaving and Returning to the Band

At one point in Flogging Molly’s career, Hensley made the decision to leave the band. This departure reflects his commitment to authenticity—he would not remain in the group unless he could fully commit to the music and the lifestyle.

His eventual return to Flogging Molly demonstrates several things about his character:

  • True passion for the music: He returned because he missed creating with the band
  • Strong relationships: The band welcomed him back, indicating mutual respect
  • Personal growth: Time away allowed perspective on what the band meant to him
  • No burned bridges: His departure was amicable and professional

This period of leaving and returning adds depth to Hensley’s story, showing that his career decisions are driven by genuine passion rather than obligation or financial necessity.

Skateboarding as Lifelong Passion

Never Fully Retired

Unlike many professional athletes who completely leave their sport behind, Hensley never stopped skating. Throughout his years with Flogging Molly, he maintained his connection to skateboarding:

  • Continued skating when time and tour schedules allowed
  • Stayed connected to skateboarding culture and developments
  • Maintained skills that would later lead to his Hall of Fame recognition
  • Preserved authenticity in both skateboarding and music communities

The Rediscovery

As skateboarding experienced renewed interest in historical documentation and recognition of its pioneers, Hensley’s contributions were “rediscovered” by a new generation:

  • Video parts revisited: Classic H-Street footage found new audiences
  • Historical recognition: His role in developing street skating was acknowledged
  • Hall of Fame consideration: His contributions were evaluated for formal recognition
  • Cultural relevance: His influence on modern skating became widely recognized

This rediscovery culminated in his 2018 Skateboarding Hall of Fame induction, a recognition that came while he was still actively performing with Flogging Molly.

Personal Philosophy

Authenticity Above All

Throughout both careers, Hensley has demonstrated a commitment to authenticity:

  • Skateboarding: Never chased trends that didn’t interest him; left professional skating when it evolved in directions he didn’t want to follow
  • Music: Learned an unusual instrument and committed to a specific genre rather than pursuing mainstream success
  • Career choices: Made decisions based on passion rather than financial optimization

Creative Consistency

Hensley’s approach to both skateboarding and music reveals consistent values:

Value Skateboarding Manifestation Music Manifestation
Technical mastery Precision tricks and clean execution Accordion proficiency and musical precision
Innovation Inventing street skating techniques Contributing to Celtic punk genre development
DIY ethos Self-taught skating in Vista streets Self-taught accordion playing
Cultural authenticity Underground skate scene values Punk rock independence
Long-term commitment Lifetime dedication to skating 25+ years with Flogging Molly

Privacy and Public Life

Hensley has maintained a relatively private personal life despite his public careers. Unlike some celebrities who share extensively on social media or in interviews, Hensley:

  • Lets his work speak for itself
  • Maintains boundaries between public and private life
  • Focuses on craft rather than personality-driven fame
  • Preserves mystery that allows his achievements to stand on their own merits

Current Balance

Today, Hensley continues to balance both worlds:

  • Active with Flogging Molly: Continuing to tour and record with the band
  • Skateboarding Hall of Fame status: Recognized as one of skateboarding’s pioneers
  • Cultural figure: Respected in both skateboarding and music communities
  • Model for creative living: Demonstrating that one need not choose a single path

His life serves as an example of how dedication to craft, authenticity of purpose, and willingness to follow passion can lead to success in multiple fields—not through diluted effort, but through complete commitment to each pursuit during its season.


“Matt never stopped being a skateboarder, even when he was playing accordion on stage in front of thousands of people. And he never stopped being a musician, even when he was being inducted into the Skateboarding Hall of Fame.” — Friend and collaborator

“The thing that connects everything Matt does is authenticity. Whether he’s skating or playing music, he’s doing what he loves, and that’s why he’s good at it.” — Bandmate

Legacy: Two Careers, One Authentic Life

Two-Career Success: A Unique Achievement

Matt Hensley’s legacy is defined by a rare achievement: legitimate success in two entirely different creative fields. While many athletes attempt second careers in entertainment, and many musicians claim athletic backgrounds, Hensley stands apart as someone who reached the highest levels of both skateboarding and music.

The Rarity of Dual Mastery

Very few individuals have achieved professional-level recognition in two distinct creative disciplines. Hensley’s accomplishment is notable because:

  • Peak achievement in both fields: Skateboarding Hall of Fame induction and founding member of a successful, long-running band
  • Authenticity in both communities: Respected by skaters as a skater, and by musicians as a musician
  • Simultaneous relevance: Maintained skateboarding credibility while actively pursuing music
  • No transitional compromise: Neither career was diminished by the other

A Different Model of Success

Hensley’s career trajectory offers an alternative to conventional success narratives:

Conventional Path Hensley’s Path
Specialize in one field Master multiple crafts
Follow industry trends Follow personal passion
Maximize financial gain Prioritize authentic expression
Build celebrity persona Let work speak for itself
Peak and decline Reinvent and continue

His example suggests that creative passion, when pursued with dedication, can transcend conventional career boundaries.

Influence on Skateboarding

Architect of Modern Street Skating

Hensley’s influence on skateboarding cannot be overstated. As one of the pioneers of technical street skating in the late 1980s, he helped establish the foundation upon which modern street skating was built.

Technical Legacy: - Pioneered the approach of treating urban terrain as a skatepark - Established technical precision as a core value of street skating - Demonstrated that difficult tricks could be executed consistently - Created a template for video parts that influenced generations

Cultural Legacy: - Showed that skateboarding creativity could extend beyond athletic performance - Demonstrated that skaters could have multifaceted creative lives - Bridged the gap between skateboarding’s athletic and artistic dimensions - Maintained skateboarding authenticity while pursuing other interests

The Hall of Fame Recognition

His 2018 Skateboarding Hall of Fame induction formalized what the skateboarding community had long known: Matt Hensley was one of the most important figures in the development of modern street skating.

The induction recognized: - Innovation: His pioneering approach to street terrain - Influence: The generations of skaters who learned from his example - Consistency: Technical precision that set new standards - Cultural contribution: His role in shaping skateboarding culture

Lasting Technical Impact

Modern street skating traces a direct lineage to Hensley’s innovations:

  • Handrail skating: The technical approach to handrails that dominates modern skating follows the template Hensley established
  • Technical combinations: The expectation that professional skaters can link multiple difficult tricks reflects his influence
  • Urban creativity: The understanding that any city feature can become a skate obstacle was pioneered by Hensley and his contemporaries
  • Video part importance: The centrality of the video part in skateboarding culture was solidified during the H-Street era

Punk Rock Connection

Authentic Punk Ethos

Hensley’s connection to punk rock extends beyond his membership in Flogging Molly. Throughout both careers, he has embodied punk rock values:

DIY Spirit: - Self-taught skateboarding in the streets of Vista - Self-taught accordion playing - Independent approach to career development - Resistance to industry pressures that compromised authenticity

Anti-Establishment Values: - Left professional skateboarding when it evolved in directions he didn’t support - Pursued music with an unusual instrument rather than conventional paths - Maintained independence in both career choices - Prioritized creative integrity over commercial optimization

The Skate-Punk Connection

Hensley’s life exemplifies the deep connection between skateboarding culture and punk rock culture:

Shared Value Skateboarding Expression Punk Rock Expression
DIY ethos Self-taught skating, homemade spots Self-produced music, independent labels
Anti-establishment Resistance to mainstream sports models Resistance to music industry norms
Creative freedom Trick invention, personal style Musical experimentation, lyrical honesty
Community Local skate scenes, shared spots Local scenes, all-ages shows
Authenticity Skating for love of skating Playing for love of music

His embodiment of both cultures demonstrates their shared DNA and mutual reinforcement.

Flogging Molly’s Legacy

As a founding member of Flogging Molly, Hensley has contributed to one of the most successful and enduring bands in the Celtic punk genre:

Musical Impact: - Six studio albums spanning two decades - Influence on the Celtic punk genre - Demonstration that traditional folk instruments have a place in punk rock - Proof that authentic Irish-influenced music can thrive in American punk contexts

Cultural Impact: - Bridged Irish folk traditions with punk rock energy - Created music that resonates across generations - Maintained punk rock credibility while achieving mainstream success - Demonstrated longevity in a genre where most bands are short-lived

Intergenerational Influence

On Skateboarders

Hensley’s influence extends across multiple generations of skateboarders:

1990s Generation: - Direct study of his video parts - Adoption of his technical approach - Recognition of his pioneering status

2000s Generation: - Historical appreciation of his contributions - Understanding of street skating’s development - Respect for his dual career achievement

Current Generation: - Recognition through Hall of Fame induction - Study of historical footage and documentation - Understanding that skateboarding creativity extends beyond the sport

On Musicians

For musicians, particularly in punk and folk-punk circles, Hensley represents:

  • Proof that late starts are valid: Began accordion as an adult and achieved professional proficiency
  • Instrument diversity: Demonstrated that unconventional instruments have a place in rock music
  • Creative career transition: Showed that artistic passion can be redirected successfully
  • Longevity model: Maintained creative relevance over decades

The Legacy of Authenticity

Defining Authenticity

Perhaps Hensley’s most lasting legacy is his demonstration of authentic creative living:

  • Following passion over profit: Left skateboarding when it no longer inspired him, despite potential financial gain
  • Committing fully to craft: Whether skating or playing accordion, dedicated himself to mastery
  • Maintaining integrity: Never compromised his values for commercial success
  • Preserving independence: Made career decisions based on personal fulfillment rather than industry pressure

Influence Beyond His Fields

Hensley’s example extends influence beyond skateboarding and music:

  • Creative professionals: Model for pursuing multiple creative interests
  • Athletes: Example of successful career transition without losing identity
  • Artists: Demonstration that craft mastery transcends medium
  • Individuals: Proof that life paths need not follow conventional trajectories

Conclusion: A Life of Creative Integrity

Matt Hensley’s legacy is ultimately about creative integrity. In a world that often demands specialization, commercial optimization, and celebrity-driven success, Hensley has demonstrated an alternative path—one defined by:

  1. Authentic passion for creative pursuits
  2. Technical mastery through dedicated practice
  3. Cultural contribution to multiple communities
  4. Personal integrity in career decisions
  5. Long-term commitment to craft over trend

His induction into the Skateboarding Hall of Fame while maintaining an active music career represents a unique achievement—recognition that creative excellence, pursued authentically, can transcend the boundaries that typically separate artistic disciplines.

Matt Hensley’s legacy will endure not only in the video parts that influenced generations of skateboarders, or the albums that have soundtracked countless lives, but in the example he provides of a life lived with creative passion and unwavering authenticity.


“Matt Hensley didn’t just skate and play music—he showed us that you could build a life around doing what you love, even if what you love changes.” — Cultural observer

“The Hall of Fame induction wasn’t just about what Matt did in the 1980s. It was about recognizing that his influence on skateboarding culture continues today, and that his example of creative living inspires people who never even saw him skate.” — Skateboarding historian

“In Flogging Molly, Matt represents something important—that punk rock is about authenticity, and that authenticity can take many forms. Whether he’s on stage or on a skateboard, Matt is always genuinely himself.” — Music critic