All 18 of Ben Stiller’s Sitcom Guest Spots, Ranked

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All 18 of Ben Stiller’s Sitcom Guest Spots, Ranked

For one of the world’s biggest comedy movie stars (Don’t believe us? Watch the clip from Extras, below, and he’ll tell you himself), Ben Stiller sure loves to cameo on situation comedies. The paychecks are probably okay, and since he’s playing himself half the time, it’s easy money! Big, fat paycheck or not, here’s our definitive ranking of four decades’ worth of Stiller guest gags, from “phoning it in” to “Bluth-tastic!”

Frasier — Barry

Grub Street Productions

Hello celebrity caller, you now qualify for SAG health insurance.

It wasn’t unusual for celebrities to do faceless call-ins to Frasier’s self-help radio show. Heck, on this episode, “Miracle on Third or Fourth Street,” alone, anonymous Eric Stoltz, Mel Brooks and Rosemary Clooney also dial in. But as Stiller comedy turns go, this one is pretty mild. We’re guessing most viewers had no idea that caller Barry was Ben. Can you actually get residual checks for this? 

Haters Back Off! — Ben Stiller

Brightlight Pictures

This still frame is pretty much the whole cameo.

On this low-profile Netflix series, Stiller plays himself, again (literally) phoning it in to ask series star Miranda to speak at his dead uncle’s funeral. Seriously, what is Stiller doing here? He appears on camera for about four seconds, looking as dumbfounded as viewers must have been when he appears out of nowhere only to vanish for the rest of the episode. Beats out Frasier only because he bothers to show his face.

Burning Love — Joe Rutherford

Stiller was a producer on Burning Love, a show that started online at Yahoo! Screen’s Comedy Channel. Remember that one? Right, we don’t either. But Burning Love was a pretty funny spoof of shows like The Bachelor, starring The State’s Ken Marino as a firefighter looking for lust. Stiller shows up briefly as Joe Rutherford, the previous season’s big winner. If you don’t blink, you can catch Stiller and his wife Christine Taylor in the trailer.

Kate and Allie — Peter

There’s nothing particularly funny about Stiller as Peter, an earnest leader of a group of sleepy student protestors. Nonetheless it’s notable because a) ohmygod, Ben is a BABY!; and b) if IMDb is to be believed, this is Stiller’s first-ever screen credit.  

Dr. Katz, Professional Therapist — Ben Stiller

HBO

I'm not funny, I'm just drawn that way.

Now we’re starting to get funny. Stiller sits on Dr. Katz’s couch to complain about his famous parents, who just happen to be the comedy team of Jerry Stiller and Anne Meara. They’re always performing around the house, Stiller kvetches. But is that closed-door argument an impending divorce or a nightclub bit? It’s very confusing to grow up in a house where you don’t know where comedy ends and reality begins. And while we wouldn’t exactly call it child abuse, Stiller still seems scarred from his parents making him play a sibling violin duet on The Mike Douglas Show

Friends — Tommy Two-Face

Jealous Ross tells Rachel she should stop dating new boyfriend Tommy (Stiller). He’s a mean guy! But no one believes Ross because Tommy is such a two-face — sweet as pie to Rachel and the gang, snarling and furious with others (including Ross) who he calls idiots. Tommy doesn’t rank higher on the list because Stiller does such a convincing job of playing the a-hole. Tommy Two-Face is incredibly unlikable, whether he’s kissing ass with Chandler or screaming at Joey’s duck.

Curb Your Enthusiasm — Ben Stiller

You probably don’t need to watch the clip to know how this one goes — Larry does something rude or annoying, Celebrity Guest (this time, Stiller) calls him out, screaming ensues. This time, Stiller and his aforementioned wife Christine Taylor offer Larry a ride to the studio. When Stiller drops off Taylor at yoga class, Larry refuses to move to the front seat. What does Stiller look like, a chauffeur? “Get in the f***ing front seat!” Funny enough, but there are better showcases for Stiller’s comic gifts.

The Simpsons — Garth Motherloving

Gracie Films

He sleeps with Marge! Just kidding, but that would have been nuts, right?

Stiller is Garth Motherloving, big boss at Motherloving Sugar Corporation. This candy conglomerate is making Springfield the fattest city in the world, not that Motherloving cares. He’s only in it for the money! Stiller plays it all low-key, and the character is funny enough. The problem is that by Season 13, The Simpsons had already played the evil CEO card several times; Hank Scorpio and Montgomery Burns are just two examples of when the show did it better.

Undeclared — Rex

Rex is a long-haired doofus who’s always in danger of falling off some kind of wagon, with potential addictions to drugs, alcohol and Steak-umms. He also happens to be Eric’s (Jason Segel) ex-stepdad, with a mullet that explains everything about why Eric’s mom ditched him. If you’ve got a few hours, ask Rex about his tattoos. 

Workaholics — Del Jacobson

When the guys don’t have enough money to pay the rent, they organize an underground wrestling show to raise some cash. One problem: Landlord Del (Stiller) won’t allow it. Eviction looms as the show goes on anyway — until they start busting folding chairs over Del’s back. Mayhem!

Mail Order Comedy

The Stiller Sleeperhold

It’s a heel turn for the ages. Or is it?

Another Period — Charles Ponzi

Riki Lindhome and Natasha Leggero star as the Bellacourts, the first family of Newport, Rhode Island at the turn of the 20th century. The period sitcom — we guess there’s such a thing as period sitcoms? — gave the Bellacourts the opportunity to hobnob with any number of historical figures, including Stiller as Charles Ponzi, creator of the Ponzi scheme. Don’t you want to get in on the ground floor?

Extras — Ben Stiller

Yet another example of Ben Stiller guest-starring as Ben Stiller. What range, this guy! This is one of our favorites, with Stiller playing an exaggerated (we assume) version of his most egotistical self. He’s directing a film here, and when Andy Millman (Ricky Gervais) refuses to take any more of his insults, Stiller lashes out with a rundown of his box-office grosses. Who knew Along Came Polly was such a blockbuster back in the day?

The King of Queens — Jerry

With the blustery breeze of Seinfeld filling his sails, Stiller’s pop Jerry Stiller was able to milk playing Jerry Stiller for several more seasons, this time as Arthur on King of Queens. In this episode, Arthur agrees to see a therapist, played by the oh-how-far-they-have-fallen William Hurt. Weird! As Hurt headshrinks Arthur back to his childhood, he has memories of his father, Jerry, played by Ben Stiller as a sibling-favoring, borderline-abusive dandy. Hoo boy, Freud would have a field day with this one. 

NewsRadio — Vic

Nothing substantial here, but Stiller is hilarious as a health club membership salesman trying to convince Andy Dick and Phil Hartman to sign on the dotted line. He’s the kind of guy who will generously knock 30 percent off the membership price, without ever telling you how much the dang thing costs in the first place.

Eagleheart — Silly Sammy

Eagleheart was an Adult Swim oddity from the early 2010s, starring Chris Elliott as a deranged U.S. Marshall. But Elliott had nothing on Silly Sammy, a kids’ show host who came on after your parents were asleep with instructions on how to harvest their internal organs. Dark and weird, just the way we like our Stiller served.

The Larry Sanders Show — Ben Stiller

HBO

Stiller is Ben Stiller once again, not quite the egotistical jerkweed from Extras but close enough. Now it’s not box office success that drives Stiller’s ego — it’s his place on People’s Sexiest Men Alive list. When Larry finds his way onto the list by getting the mag to bump Stiller, it’s on. Despite the presence of a live audience, Stiller has no problem shouting “Larry Sanders, the big asshole man!” to anyone who will listen. This might be the only time in Sanders history where Larry actually throws a punch! So sad that Artie had to break it up because we’d love to see this brawl to end ‘em all.

Freaks and Geeks — Agent Meara

With Vice President George Bush visiting William McKinley High School, Special Agent Meara (Stiller, in a nice nod to his mom, Anne) is assigned to security detail. He immediately sniffs out Jeff, the school guidance counselor, as a potential problem “with a real Dr. Feelgood look.” 

But it turns out the officious prick isn’t happy with his work, ultimately seeking out Jeff’s advice about his future. Jeff suggests a career aptitude test to see where Meara’s real talents might lie: “Do you like working with major appliances? That’d be a yes.”

Arrested Development — Tony Wonder

Since he appears in multiple magically delicious episodes, Stiller’s Tony Wonder is maybe overqualified for a “guest spot.” But the flashy magician is a great comic rival (and eventual romantic interest) for G.O.B., a performer who got a spread in Poof! magazine by baking himself into a giant sandwich to feed the troops. The role is educational as well, reminding viewers that “you don’t want a hungry dove down your pants. That’s how Tony Wonder lost a nut.”

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