'21 Jump Street' Turns 30: 12 Guest Stars Whose Careers Are Still Rad

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21 Jump Street - Josh Brolin

Josh Brolin, Season 1, “My Future’s So Bright, I Gotta Wear Shades”

Brolin lost out on the role of Hanson to Depp, but he did appear early in the show’s run as part of a trio of smug, drug-smuggling preppies suspected of raping and murdering a girl from the other side of the tracks. His character rats out his pals but gets offed in the end by the victim’s brother.

Quote: “Hey, no risk, no rush!”

21 Jump Street - Blair Underwood

Blair Underwood, Season 1, “Gotta Finish the Riff”

In one of his earliest roles, Underwood plays a gang leader slapped around by a school principal. He and his minions take the entire high school hostage at gunpoint in retribution. Hoffs, undercover as a gum-cracking bad girl, gets her man in the end.

Quote: “See, these are my brothers. This is my blood. They do a light time. I just disappear right down the night line.”

21 Jump Street - Jason Priestley

Jason Priestley, Season 1, “Mean Streets and Pastel Houses”

Three years before clean-cut Brandon Walsh, Priestley went hardcore as a suburban punk named Tober who faces off against a rival gang. Priestley also appeared as a different character in the season 2 episode “Two for the Road,” which also featured Pauly Shore.

Quote: “My ‘rents didn’t name me Tober … Names other people give you, they just aren’t important … It’s my favorite month. October, man. It’s when everything dies.”

21 Jump Street - Christina Applegate

Christina Applegate, Season 2, “I’m Okay, You Need Work”

A year after debuting as Kelly Bundy on Married With Children, the quintessential bleached blond is a manipulative patient at an in-patient drug and alcohol treatment center being investigated for abuse.

Quote: “Man, you’re really gorgeous. When did you get here? And when are you leaving?”

21 Jump Street - Peter Berg

Peter Berg, Season 2, “Champagne High”

In his acting debut, Berg is a letterman shaking down and tormenting a young dweeb (played by Andrew Koenig, the future Boner of Growing Pains), who turns to Penhall for protection.

Quote: “Come here, I tell you what, you been a good boy today, Wally, a really good boy. Today you skip the wedgie.”

21 Jump Street - Brad Pitt

Brad PItt, Season 2, “Best Years of Your Life”

This very special episode is about teen suicide — a student Hanson and Penhall bust winds up killing himself, and no one, including Pitt as the kid’s somewhat callous buddy, knows how to talk about it.

Quote: “Yeah, and there was homework. We have to stay alive until tomorrow. Sort of a pass/fail assignment?”

21 Jump Street - Christopher Titus

Christopher Titus, Season 3, “Wooly Bullies”

Penhall is attempting to infiltrate a group of computer hackers (“I have a Macintosh 2 with extended memory!”) to discover they’re being targeted by a bully. Back at Jump Street, he recalls being bulled in his school by Jack, played by Titus in his first TV role, who steals Penhall’s cherry red Cadillac and his girl at a dance.

Quote: “Well, hey, hey, hey, what do we have here? Rad-looking wheels, Penpal … Hey, this thing get FM?”

21 Jump Street - Bridget Fonda

Bridget Fonda, Season 3, “Blinded by the Thousand Points of Light”

Fonda, who had just wrapped the films Scandal and Shag, plays a sensitive homeless teen whom Hoffs convinces to return to her family.

Quote: “I was never a whore. I do it for drugs, but never for money.”

21 Jump Street - Vince Vaughn

Vince Vaughn, Season 4, “Mike’s P.O.V.”

In only his second acting gig, Vaughn plays a friend of a student (Donovan Leitch) who is struggling with guilt after he was hired by a teacher to shoot his wife.

Quote: “Whoa! What if Mrs. Tompkins was trying to kill her husband and the guy double-crossed her?”

21 Jump Street - Rosie Perez

Rosie Perez, Season 4, “2245”

Perez’s follow-up to her sassy Do the Right Thing turn is as Rosie, the sassy girlfriend of a drug dealer who kills an undercover Jump Street cop. Then the pair try to knock over a convenience store, but she winds up shooting the clerk to death when she thinks he’s reaching for a gun.

Quote: “That wasn’t a date. That was being mauled by some slime named Vic.”

21 Jump Street - Kareem Abdul-Jabbar

Kareem Abdul-Jabbar, Season 4, “Hi Mom”

The basketball legend plays the principled new athletic director of a state university where a cover-up of the drug-related death of a star athlete is underway, along with grade fixing, illegal scouting and other ethical no-nos.

Quote: “There’s nothing in my experience, either on the court or off it, that can prepare you for a tragedy like this, except to say that these young men, these warriors, are indeed mortal.”

Jada Pinket Smith - 21 Jump Street

Jada Pinkett Smith, Season 5, “Homegirls”

In the last episode of the series, Hoffs investigates a drive-by shooting of a female gang member and befriends one of her soft-hearted friends, played by Pinkett, who yearns for a life outside the ‘hood.

Quote: “Look, you could come cut my other eye out. I’m outta here!”

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Fox's early hit 21 Jump Street turns 30 on April 12, 2017. The police procedural about baby-faced undercover cops in high school has not aged particularly well, from the corny villains to the straining-to-be-cool dialogue to the barely-edifying PSAs ("The point is, drugs can really mess you up!") to all those feathered earrings. It was very '80s.

While Johnny Depp, who played Tom Hanson, was the main breakout star, 21 Jump Street failed to launch the rest of its original cast—Holly Robinson Peete as Judy Hoffs, Peter DeLuise as Doug Penhall, Dustin Nguyen as H.T. Ioki—into the Hollywood stratosphere, it did give early boosts to a number of actors who have, in fact, aged exceedingly well.

Click through the gallery above for an awesome flashback through the '80s.

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