William Strobeck and Gus Van Sant are both legends in their own creative fields, and are regarded as hugely influential figures in the world of filmmaking. Through different lenses, their work focuses on the countercultural subsections of youth, street culture, and what is generally seen as taboo subject matters within mainstream society. In March of 2025, Van Sant connected with Strobeck over the phone from his home in Los Angeles for a conversation featured in issue 10 of Living Proof Magazine.
Gus Van Sant was born in Louisville, Kentucky, though his father’s job as a travelling salesman resulted in his family moving a number of times during his early years. He finished high school in Portland, Oregon – a city he would frequently revisit in his work as a director. His early interest in film led him to Rhode Island for school, earning a Bachelor of Fine Arts degree before moving to Los Angeles and working in Hollywood as a production assistant. He then moved to New York City, where he directed commercials for an advertising agency, and afterwards went back to Portland, where he filmed his directorial debut: Mala Noche (1986).
In the following years while living in Portland, Van Sant released a number of independent films, including Drugstore Cowboy (1989) starring Matt Dillon and William S. Burroughs, as well as My Own Private Idaho (1991) with Keanu Reeves and River Phoenix. Both films, now considered cult classics, dealt with topics such as robberies, drug addiction, street youth, and same-sex romance.
In 1995, Van Sant directed To Die For, starring Nicole Kidman, Matt Dillon, and Joaquin Phoenix, and served as a producer on the set of Larry Clark’s directorial debut Kids, a coming of age drama written by Harmony Korine. Clark and Korine casted teens in New York City with no prior acting experience, starring Leo Fitzpatrick, Justin Pierce and Chloe Sevingy — many of whom hung around or worked at Supreme during the early days of the skate shop. Upon release, Kids would become hugely influential amongst young skaters across the country, including a teenaged William Strobeck living in Syracuse, New York.
Strobeck, who had already begun skateboarding and filming his friends in Syracuse, would move to Philadelphia the next year at age 17, where he frequented the legendary Love Park, skating and filming with his newly-acquired VX1000. As the Philly scene grew, Strobeck was approached by Alien Workshop to film for their upcoming video Photosynthesis. He quit his job at a local pizza shop and dropped out of school, marking the beginning of his career as a professional skate filmer.
When Love Park closed to skaters in the early 2000’s due to bans and renovations, Strobeck moved to New York City, and continued filming for Alien Workshop. With no other job aside from filming, Strobeck became immersed in the city’s downtown scene.
Around the same time, Van Sant was bouncing between mainstream success and independent arthouse cinema. In 1997, he directed Good Will Hunting, written by and starring Ben Affleck and Matt Damon. He later recorded and released two albums, published a novel, and spent the next few years working on a series of films based on real-life tragedies, often referred to as his “Death Trilogy.” The first of these was 2002’s Gerry, starring Casey Affleck and Matt Damon, which was inspired by the death of a hiker in New Mexico who was allegedly mercy-killed by his accomplice after the pair got lost in the desert.
His next film released the following year, Elephant, was based heavily on the Columbine High School massacre. The film was seen as highly controversial upon release for its violent depiction of the events which occured only a few years prior, but was awarded the Palme d’Or for best feature film at the 2003 Cannes Film Festival. The final film of the trilogy, Last Days (2005), was loosely based on the final days leading up to the suicide of Nirvana frontman Kurt Cobain.
Following the trilogy, Van Sant released Paranoid Park (2007), adapted from a novel of the same name. The film follows a teenage skater in Portland who accidentally kills a security guard while attempting to hop a freight train. Van Sant – who was a skater himself in his youth in Portland during the initial craze of the ‘60s – used a MySpace page to cast teenagers with no prior acting experience, and gave the lead role to a skater who initially auditioned as an extra. Today, Paranoid Park is considered a cult classic in the world of skate movies, along with Larry Clark’s Kids and Wassup Rockers (2005).
Back in New York, Strobeck continued his film work, producing skate videos and frequently working with Mark Gonzales. Eventually, he was approached by Supreme to film buddy (2012), a 50-second commercial featuring Jason Dill and Tyshawn Jones. The video opens with an old man on the street urging a then 13 year-old Tyshawn Jones to show him a trick before cutting to him frontside over-crooking a rail, and ends with Dill and a passerby discussing smoking crack. Strobeck’s tendency to keep the camera rolling during the candid moments that inevitably come along with street skating in the city, and cutting them in with his skate footage offered a taste of what was to come in Supreme’s upcoming full-length video, which he began filming that same year.
The release of cherry in 2014 was a pivotal moment in the culture, and undeniably changed the look of skateboarding on a worldwide level. Much like the film’s soundtrack, which mixed the contemporary works of Chief Keef and Salem with classics from Raekwon, Jane’s Addiction and The Cure, the video featured a number of already household-name skaters, while also introducing the world to a cast of teens who would become the future faces of Supreme. Established legends like Mark Gonzales, Jason Dill, Alex Olson and Dylan Rieder skated alongside Tyshawn Jones, Sage Elsesser, Na-Kel Smith, Kevin Bradley, Aiden Mackey and Sean Pablo, a generation of future stars who became the catalysts for a new modern era of post-cherry skateboarding.
Strobeck’s auteurship was hugely influential, and marked the beginning of a noticeable evolution of the way skateboarding was filmed moving forward. Rather than making the viewer feel they were watching a series of practiced stunts, his video provided the feeling of being there with the Supreme crew for every try, running through train stations from spot to spot, encouraging a stranger to ghost a hit from their crack pipe, and coming back with Mark Gonzales to repaint a building he scuffed doing a wallride. With the quickly rising popularity of Supreme’s clothing within the 2010’s streetwear and hip-hop cultures, cherry transcended the reach of a typical skate video, bringing the effortlessly cool styles of the skaters to a greater audience across the globe, who quickly looked to recreate what they saw showcased in New York City. Sales of Converse Chuck Taylors surged, and soon popped up in skate videos which mimicked Strobeck’s zoom-heavy style of cinematography, as well as his editing which elevated their surroundings, the vibes of the session, and the B-roll antics to the same level of importance as the skateboarding itself.
Since cherry, Strobeck has released a number of videos with Supreme, including feature-length edits BLESSED (2018), CANDYLAND (2019) and STALLION (2021). Gus Van Sant continues to produce films while living in Los Angeles, and is currently in production on his next film Dead Man’s Wire, based on the true story of a 5-million-dollar hostage situation with a mortgage broker in Indiana.
In Issue 10 of Living Proof Magazine, Strobeck and Van Sant discuss skateboarding, finding inspiration, filmmaking, the legacy of Kids, and more. Full interview available only in-print.
This story was written by Eden DaSilva for the release of Issue 10 of Living Proof Magazine. Now available on our Patreon and Online Shop.
