Top 20 Most Surprising Sitcom Cameos

Top 20 Surprising Sitcom Cameos

Welcome to MsMojo, and today we’re counting down our picks for the Top 20 Surprising Sitcom Cameos. For this list, we’ll be looking at the most shocking appearances from some of our favorite celebrities on our favorite funny television shows. We’ll be focusing on live-action shows for this list, so apologies to anyone whose favorite cameos include Tony Blair on “The Simpsons.” Watch out for some cameo-related spoilers ahead, and let us know if we missed any of your favorites in the comments below. First and foremost, Britney Spears is a pop star. But for a majority of her career, Spears has seemed to have a genuine interest in acting. Still, we’re not so used to seeing the singer act like anyone but herself, making her cameo in “How I Met Your Mother” all the more surprising. The show has certainly featured other celebrity cameos (Kim Kardashian comes to mind). But what makes Spears’ run on the sitcom so funny is the character she’s asked to play. Spears plays Abby, who is infatuated with Josh Radnor’s Ted. No offense to Radnor, but the idea of the pop princess obsessing over Ted Mosby is hilarious. It would be pretty cool to drive a celebrity’s old car around. That’s the premise of this particular “Seinfeld” bit. During a season six episode, George buys a car solely because he believes it was once owned by actor Jon Voight. Jerry quickly squashes that dream with a quick peek through the glove compartment, but all hope is not lost! The real Jon Voight shows up a bit later in the episode when Kramer sees him in a taxi. Kramer tries to clear up whether the car really did belong to Voight, but his inquiry is crushed when Voight literally bites him. This is such a silly cameo for an actor to have, and we respect Voight for taking it as seriously as he did. What’s the point in dating Julio Iglesias if nobody knows you’re dating Julio Iglesias? According to Sophia from “The Golden Girls,” there is no point. This legendary sitcom takes place in Miami, so it makes sense that another Miami legend would make an appearance for a very special episode. The Spanish singer made an appearance in season four when Sophia needed a very sultry Valentine’s Day date. And who better to pick to fit the fill for the word sultry? The Spanish crooner absolutely charms the pants off of everyone, including the audience, who can’t stop screaming when he walks on stage. If we’re being honest, every single cameo on the television show “Extras” made us wonder how in the world they got that person to get on board. The show stars Ricky Gervais as a background actor on sets, and each episode features a different celebrity. From Ben Stiller to Daniel Radcliffe, you’d be surprised how many famous people have been a part of this sitcom. But our favorite cameo comes from Sir Patrick Stewart himself. In his episode, Stewart is an incredibly crass version of himself. The storyline features Stewart working on a script about a man who can undress women using only his brain. Luckily in real life, we don’t think Stewart is quite that gross. Kim Kardashian is no stranger to cameos. From “Ocean’s 8” to “90210” to “30 Rock,” Kardashian has appeared as herself in plenty of movies and television shows. So, it’s not so much the fact that she did a cameo that’s so surprising here. It’s more about which show she appeared on. In its first season, “Last Man Standing” features a cameo from the middle Kardashian sister. This sitcom stars Tim Allen as a father of three who runs a sports store based in Denver. We don’t know about you, but to us, this doesn’t scream Kardashian. If Kim’s audience was tuning in to see her on “Last Man Standing” in the early 2010s, we would be shocked to hear about it. There have been plenty of musicians who have shown up on episodes of “Jane the Virgin.” From Gloria Estefan to Britney Spears, the telenovela was no stranger to pop stars. However, some pop star cameos were sneakier than others. While those two ladies played themselves, Kesha dropped by the set for an actual character role. In season two, Kesha appears as Jane’s annoying next-door neighbor who has no regard for infants and their strict sleep schedules. The show does poke at Kesha’s pop star status by making her a struggling musician, but for the most part, it doesn’t call attention to her fame. The show lets her actually act, and you know what? She’s not too shabby! Yeah, yeah. We know you’re all probably thinking about that famous Bruce Willis cameo on “Friends.” While Paul certainly is the man, we think this earlier cameo in Willis’ career takes the cake. In a first season episode of “Roseanne,” Bruce Willis randomly walks into Roseanne’s room and joins her in bed. She reacts as we all would, and begins to scream and hug him. “Roseanne” started in 1988, which would have been the same year as “Die Hard” and at the tail end of Willis’s show “Moonlighting.” In other words, he was a huge star at the time. Charlie Sheen, Elvis Costello, and Harry Dean Stanton. Sounds like members of a men’s support group to us! In an early episode of “Two and a Half Men,” Sheen’s character hosts a men’s group at his home that his brother desperately wants into. However, there’s one member of this particular group that we really can’t believe showed up to the set. Famous actor and multiple Oscar winner Sean Penn is the last elusive member of Sheen’s group. This episode would have aired after Penn won his Academy Award for “Mystic River,” and we honestly can’t believe he agreed to be on a sitcom. But we’re glad he did. This is one of the longer cameo arcs on this list, and honestly, we’re not sure if Charlize Theron would agree to the role today. But the details of this particular cameo make it all the more shocking that it actually happened. In season three of “Arrested Development,” Theron shows up as Michael’s love interest. By this point in her career, Theron was acclaimed for roles in films such as “The Cider House Rules” and “Monster,” the latter for which she won an Oscar. But in “Arrested Development,” she plays a woman with developmental issues who becomes the butt of the joke. Looking back, it’s a pretty wild storyline that few would touch now. In his later years, The Rock has really leaned into his tough guy image, making action movie after action movie. But we also remember his earlier run in family entertainment like “The Game Plan,” “Tooth Fairy,” and of course, his cameo on “Hannah Montana.” In the episode, The Rock plays himself, and Miley and Lilly team up to try and get an embarrassing photo of him in an effort to stop Miley’s identity of Hannah Montana from being revealed. The girls give The Rock a makeover in order to achieve this goal. The Rock is actually incredibly funny in this episode, and handles everything thrown at him in good stride. Also? The makeover looks great. In the late 1990s and early 2000s, Matt Damon was on top of the world. From “Good Will Hunting,” to “Ocean’s Eleven,” it seemed he could do anything he wanted. So, it’s very special to us that what he wanted to do was make an appearance in the fourth season of “Will & Grace.” Damon plays a straight man who pretends to be gay in order to join the Gay Men’s Chorus. Jack finds out that Damon’s character is lying, and enlists Grace to try and put that hetero back into the closet. Damon is incredibly funny in his cameo, and this seems to start his run of being willing to show up in pretty much anything. If there’s one thing we know about Liz Lemon, it’s that she loves Oprah Winfrey. She is a human being, after all. But we never thought that in real life, Oprah would decide to make a guest appearance on “30 Rock.” Yet somehow, Tina Fey worked her magic and the talk show host appeared in an episode in typically hilarious fashion. After taking a sedative to calm her down during a flight, Liz encounters Oprah on the plane. Or, who she thinks is Oprah. Turns out, Liz’s drug intake caused her to hallucinate, and who she thought was Oprah was actually a 12-year-old girl. Oprah the actress has a great time with this conceit, delivering zinger after funny zinger. Back in the day, there were some really hilarious celebrity cameos on “Friends.” Brad Pitt (Married to Jennifer Aniston at the time) makes a hysterical appearance in season eight. But one of the most surprising cameos comes from an actor best known for his dramatic chops. In season seven, Joey is chosen to officiate Monica and Chandler’s wedding, but he’s stuck on the set of a movie. The shoot is taking longer than expected because of a drunken actor, played by none other than Gary Oldman. Oldman is positively hilarious in each and every scene, slurring and spitting his way to excellence. When Michael Scott left “The Office,” we all wondered who was going to replace him. That departure brought on a slew of celebrity cameos, but the one we want to talk about today happened a bit before Steve Carell left. Idris Elba first makes an appearance in season five of “The Office” as a new no-nonsense foil to Michael Scott’s ridiculousness. This would be the first of several times Elba would appear on the show, each time subverting your expectations with this serious attitude. We were so used to seeing Elba on a show like “The Wire,” it felt fresh and exciting to see his persona on something as silly as “The Office.” If “Star Wars” characters were going to appear on a sitcom, this would be the perfect one for it. “The Big Bang Theory” has featured several “Star Wars” actors, including Mark Hamill in Season 11, and James Earl Jones in the very episode we’re going to talk about today. But while Darth Vader is a pretty exciting get for any television show, no one beats Carrie Fisher. Sheldon joins James Earl Jones for a game of ding-dong ditch at Fisher’s house. While Fisher acts as though this is something Jones has done before, this was actually the first time the actors had ever met in real life. Talk about a father/daughter reunion! Sometimes, politicians show up on your favorite dramas or even your favorite adult sitcom. But, a politician showing up on a Nickelodeon kids’ show? And not just any politician, but the First Lady herself? Now that’s surprising! But Michelle Obama did just that on the fourth season of “iCarly,” bumping and grinding her way right into our hearts. Reportedly, Obama was cast on the show as a way to promote her Joining Forces initiative. That program aims to offer support to military and veteran families. Not only is the appearance for a good cause, but Obama actually had some pretty solid comedic chops. Good stuff all around. Picture this. A guy who shared a set with Kelsey Grammer has also actually been to outer space. It’s hard to believe, but literal astronaut John Glenn actually had a small cameo on “Frasier” back in the day. In Season Eight, Glenn shows up as a guest on Frasier’s radio show. Glenn had been a senator at the time of his appearance and was game enough to make jokes at his expense. He was also more than willing to make jokes about his time in space. In the world of the show, Glenn alludes to spending time with possible extraterrestrial life in space. All the while, Frasier, in typical Frasier fashion, is completely oblivious to it all. Well played, Senator. He might not have been the president yet, but having the vice president show up on your sitcom is no joke. On “Parks and Recreation,” Leslie Knope is a true blue politician fangirl, and the show makes fun of that aspect of her personality quite often. Plenty of politicians made appearances on the show, including Michelle Obama and John McCain. But the biggest get of them all was Joe Biden. Leslie absolutely fawns over the then-vice president, but he takes it all in stride. Biden only shows up for a short amount of time, but he proves he’s got enough comedic chops to hang with the big dogs, at least for a while. Now, we know you remember this one. Perhaps in one of the most random cameos of all time, in season three of “Friends,” Billy Crystal and Robin Williams took the stage. The comedians interrupt our regularly scheduled “Friends” time at the beginning of an episode. Williams’s character has just found out his wife is cheating on him. Instead of comforting him, Crystal’s character reveals that he is the other man. It’s a hilariously bizarre moment, complete with a strange voice from Williams and great comedic timing from Crystal. But the best part about this appearance is that it wasn’t even planned. The two actors just happened to be on set that day, and agreed on the spot to film a little cameo. In a Season Three episode of “New Girl,” the gang crashes a party held at the mansion of none other than Prince himself. But if you thought this was just going to be a fun setting and conceit, you’d be wrong. Prince actually shows up in the episode and delivers a few incredibly funny scenes. The funny thing about this cameo is, apparently the “New Girl” team didn’t reach out to Prince. He reached out to THEM to ask if he could be on the show. Talk about flattery! The episode ended up being not only one of the most expensive episodes of the show, but the number one most watched in its run.