Ben Stiller is a man of many talents. Stiller, the son of actors and comedians Jerry Stiller and Anne Meara, is a comedian himself who has also done plenty of acting since making his debut in film, television, and on the stage from a very young age. Some of his more notable roles have taken place in titles such as Meet the Parents, Zoolander, Tropic Thunder, The Ben Stiller Show, and Arrested Development. The screenwriter and producer has also added director to his credentials over the years, with endeavors like the TV show Severance and the movie The Cable Guy.

Stiller has clearly created a storied (and often comedic) resume over the lengthy course of his career that has shown that the New York City-born standout hasn't been afraid to take on quite a few different opportunities. He was even a drummer during his high school years in the '80s (and again in 2018) for a post-punk rock group called Capital Punishment. Maybe it was this early participation in music that also led Stiller to appear in a wide variety of music video cameo work once he became a more established celebrity name.

5 Smash Mouth, All Star (1999)

Moments With The Mystery Men

San Jose, California rock group Smash Mouth came into being in the early '90s as a quartet consisting of guitarist Greg Camp, bassist Paul De Lisle, drummer Kevin Coleman, and lead vocalist Steve Harwell. Initially, Smash Mouth was considered to be in the ska punk style with their 1997 debut album Fush Yu Mang, but by their 1999 follow-up, Astro Lounge, they had shifted into more pop-leaning rock waters. This was the album where the band would create what's arguably their signature track, the Camp-written first single, "All Star."

Written as "a song for the misfits and the outcasts," "All Star" likely inspires either nostalgic joy or overplayed annoyance (or both), depending on the listener you ask. This was largely created by persistent radio play, as well as "All Star" being quickly licensed for films like Shrek and Mystery Men. The cult classic misfit superhero film Mystery Men is where Stiller's music video cameo comes in with "All Star," as he starred in the flick along with a cast including William H. Macy, Greg Kinnear, Eddie Izzard, and musician Tom Waits.

The "All Star" music video features stock footage of Stiller and other cast from Mystery Men as they look for new superhero recruits, expressing interest in Harwell. The rest of the video includes footage from the film as well as Harwell performing "super" feats like rescuing a dog from a burning house. The whole presentation is a bit oddly and humorously surreal, which, honestly, is pretty on par with both the lyrical structure of "All Star" and the narrative of Mystery Men.

4 Limp Bizkit, Rollin' (Air Raid Vehicle) (2000)

A Cheesy-Swaggering Joy Ride

Much like Smash Mouth, rap rock/nu metal band Limp Bizkit was another group formed in the early '90s, led by somewhat infamous frontman Fred Durst. Over the course of their history, Limp Bizkit has often walked the line between being a serious endeavor and embracing a parody of full-on, goofy, corny, white guy weirdness. That oddball side quickly comes out in the group's name, as well as the title of their 2000-released third album (where the song "Rollin' (Air Raid Vehicle)" comes from), Chocolate Starfish and the Hot Dog Flavored Water.

The LP found the group eager to expand on the mainstream success they'd recently found at the time, something they'd achieve, as Starfish would become the fastest-selling rock album upon release of all time. "Rollin' (Air Raid Vehicle)" was the record's second single, and was initially envisioned as a hip-hop track before being remixed as the hard rock, pregame sporting event pep rally fire-up most listeners would recognize it as. That frat rock feeling emanating from "Rollin'" is also present in the song's music video, which finds Stiller in a cameo as himself along with actor Stephen Dorff.

It's not exactly a heavyweight-level depth of an appearance for Stiller, but that fits the "Rollin'" song.

The pair pull up to a valet parking spot in a fancy sports car, and upon finding no valet present, Stiller tosses the keys to a nearby Durst (apparently mistaking him for one). Durst then takes the car for a joyride with his bandmates, alongside shots of the group playing on top of the World Trade Center and Durst performing in a room with backup dancers. It's not exactly a heavyweight-level depth of an appearance for Stiller, but that fits the "Rollin'" song and music video's sense of straightforward, parody rocker sensibilities.

3 Tenacious D, Tribute (2002)

An All-Holy Homage To Song Greatness

And speaking of parody rock, the early '90s came calling once again with the formation of the comedy rocker duo Tenacious D. Created by actors Jack Black and Kyle Gass (with Black on lead vocals/guitar and Gass on guitar), the pair cycle between rock opera theatrics and an often more mature, coarse sense of comedic humor on their recorded material. They released their self-titled debut album in 2001, which included their second single dubbed "Tribute."

"Tribute" (the first song written by Tenacious D) describes a story of Black and Gass meeting a demon down a long and lonesome road, and being forced to play the greatest song of all time for it so they don't lose their souls. They play the track, but forget what it is, so this song is just a "Tribute" to it. In the music video, Black and Gass begin recording "Tribute" in a cheap shopping mall karaoke booth (which feels very early 2000s) before bursting out to sing to disturbed ersby (including Stiller in a blink-or-you'll-miss-it cameo).

2 Jack Johnson, Taylor (2004)

A Laid-Back Lip Sync

While the prior music videos found Ben Stiller in more of a brief or side cameo role, that all changed with the actor's appearance in the 2004 music video for alternative/folk pop singer Jack Johnson's 2003 song "Taylor." Released as the third single from Johnson's second album, On and On, the track is a quirky yet charming tale that fits squarely in the peg of the Hawaiian singer-songwriter's typically laidback, sand-and-sandals tempo style.

The video features Stiller in more of a lead role along with Johnson, as Stiller comes to Hawaii to help Johnson create his video. Initially lip-syncing "Taylor" himself comedically with a guitar in hand, Stiller then hands the reins over to Johnson while providing over-the-top direction, props, and daydreams of himself surfing and playing the ukulele. The "Taylor" video is quite well-suited to Stiller's hammy, slightly self-absorbed, typically physical comedic style. Johnson fits well as the slightly perturbed straight man, making "Taylor" a memorable creation.

1 SZA, Drive (2024)

A Soulful Car Ride

In perhaps the most unlikely collaboration from this list, Stiller recently showed up (also in a significant role) in SZA's music video for her song "Drive." The track was released in 2024 as part of the artist's deluxe reissue of her 2022 record, SOS, called Lana. In addition to including a whole other album's worth of material (15 songs later expanded to 19), the themes of Lana explore a progression out of chaos and romantic trauma toward self-love started by SOS.

Stiller is the unexpected centerpiece of the music video that SZA wanted to be the lead.

Not that there still aren't darker, self-doubting moments. "Drive" is a guitar-led, introspective slice of soulful R&B that explores trying to find a peaceful emotional center in the midst of racing, intrusive thoughts. Stiller is the unexpected centerpiece of the music video that SZA wanted to be the lead (over wrestler John Cena), as she's reportedly a big fan of his work. He proves up to the challenge, driving a car alone at night on the road, trying to stay awake while lip-syncing the song.

Stiller winds up almost drifting off the road before snapping out of it, holding himself half outside the vehicle's window, doing doughnuts with the car, and dancing outside of it while it slowly moves before driving off again. The video then partially cuts to the next Lana track, "Crybaby," while SZA herself frolics in a field in makeup and a mask dressed to look like an insect. It's a slightly unusual video, but Ben Stiller's portion accurately fits the slow burn of "Drive" in a very fitting fashion.