A mob of Supreme-clad skateboarders lined up outside of Sunshine Cinema on Sunday for the New York premier of “Pretty Sweet,” the latest skateboarding video from the Girl and Chocolate brands. The premiere, hosted by East Third Street shop DQM, drew the likes of Kanye West, Mike D of the Beastie Boys, actor Michael Rappaport, and actor, DJ, and East Village resident Leo Fitzpatrick, star of the forthcoming “Doomsdays.”

The highly anticipated film was introduced by Rick Howard, Mike Carroll, and Spike Jonze, co-owners of Girl Skateboards. Mr. Jonze is best known as the director of features such as “Being John Malkovich” and “Adaptation,” but he cut his teeth photographing skaters, and in 1991 directed “Video Days,” a landmark skateboarding short that established a formula of cutting-edge editing techniques paired with humorous skits.

“Pretty Sweet,” filmed in HD and boasting gratuitous slow-motion steady-cam shots, is the most evolved of the videos that Mr. Jonze has released with Girl, and no wonder: it took five years to complete – a time span longer than most pro skateboarders’ careers.

Girl was formed in 1993 in Torrance, CA, in part as an escape from the increasingly high-pressure, competitive direction of skateboarding. It was meant to be a “fun little thing,” in the words of Mr. Carroll, who along with Mr. Howard is still a talented skater in his own right. But after releasing “Goldfish” in 1993, the brand has managed to build an increasing amount of buzz around each of its subsequent works.

Packed with special effects and even an Owen Wilson cameo, “Yeah Right!” (2003) was the first of the videos to pair the cinematography and editing of Ty Evans with Mr. Jonze’s whimsical skits.

Anthony Pappalardo

“Pretty Sweet,” co-directed by Mr. Evans, begins with a bang, as a slow-motion crane shot ends in a shower of confetti. The subsequent flurry of tricks, which elicited ooos and aahs from Sunday’s audience, is woven together with jump cuts, HD slow-mos, skits, and this time two celebrity cameos. Jack Black plays the “annoying filmer” – sweating, cursing, and eventually disrobing as the Girl pros try to film tricks. And Will Arnett, wearing a “#prettysweet” T-shirt, is employed to berate the team.

Mr. Arnett’s verbal jabs are intended in part to echo criticisms leveled at Girl and Chocolate by many skateboard message-board lurkers. In the aftermath of the brand’s 2007 video, “Fully Flared,” with its dramatic HD second angles and pyrotechnic opening montage, many pros voiced their unhappiness with the pressure of filming for big-production videos. It seemed Girl might have morphed into something the company had initially rallied against.

All that created a considerable amount of drama in the five years leading up to “Pretty Sweet.” Many of the Girl and Chocolate team riders were approaching their late 30s, an age at which pros rarely stay active, and rumors surfaced that the video would be a showcase for the brand’s emerging youth movement.

Anthony Pappalardo The opener, a tribute to the late Keenan Milton.

Sure enough, the video does represent Girl’s new ranks prominently, with several veteran pros featured only in shared parts (Mr. Howard didn’t have a single trick in the video).

Girl and Chocolate’s new breed is led by Street League champion Sean Malto and Mikemo Capaldi, but it’s the group of skaters known as the Trunk Boyz that truly embody skateboarding’s next generation. Rather than being bound to one discipline of skating, these young skaters show an appreciation for the entire lineage of the sport. They’ve had access to the parks, streets, ramps, and natural transitions that have changed the approach and style of the pastime.

In deference to this shift, Girl and Chocolate have amassed an impressive roster – including Vincent Alvarez, Cory Kennedy, Elijah Berle, Raven Tershy, and Stevie Perez – that could anchor their brand for the next fifteen years.

Of course, it’s possible the relative lack of veterans was an editing choice, as the stalwarts all deliver powerful footage, albeit in measured doses. Guy Mariano, for instance, is given the coveted closing part.

Mr. Mariano has had an up-and-down career, having produced some of the most prolific video parts in skateboarding’s history only to disappear from the spotlight for years at a time. It appeared skateboarding had lost a legend when Girl removed his pro model from their line amid rumors of drug abuse, but Mr. Mariano made a sober comeback in “Fully Flared.” Now 36, he’s still so naturally talented that he can lead the young progressives despite the mileage on his knees.

“Pretty Sweet” ends with an entertaining montage featuring several skateboarding luminaries (late downtown legend Harold Hunter is namechecked) as well as footage of a burning palm tree: the aftermath of a poorly aimed confetti canon from the intro.

As the crowd exited Sunday night, the comments weren’t focused on who had the best part or what the most impressive trick might have been. The general consensus was that everyone needed to see “Pretty Sweet” at least five more times to even process the complexity of this latest watershed moment in skateboarding.