Top 20 Most Surprising SNL Cameos
#20: Eminem
In a parody of Eminem’s “Stan”, Pete Davidson plays Stu, a young man with an increasingly unhealthy obsession with getting his hands on a PS5. Throughout the skit, we’re teased with potential cameos from Dido and even Elton John but, these turn out to be fellow castmates, Kate McKinnon and Bowen Yang. But even as the words “Slim Shady” flash up on Stu’s TV, we still can’t quite believe that we’re actually seeing “The Real Slim Shady”. As he unwraps a PS5, he has some choice words for Stu. This sketch was the Christmas gift we didn’t even know we wanted.
#19: Brad Pitt
In an interview, Dr. Fauci joked that he would want Brad Pitt to play him on “SNL,” and his wish was their command. In the cold opening for their “At Home” series, Pitt adopts Fauci’s recognizable voice and mannerisms to address some of the misinformation surrounding the Covid-19 pandemic … particularly those shared by a certain individual. Pitt even received an Emmy nomination for his cameo, and high praise from the Doctor himself. Before wrapping up, the actor removes his costume to pay tremendous gratitude to the real Dr. Fauci as well as everyone who has been working tirelessly on the frontlines.
#18: Judge Judy
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Cheri Oteri’s impression of this no-nonsense, badass TV Judge is one of her best and most memorable recurring characters from her SNL tenure. However, there is one person who thinks that there’s still room for improvement. Mid-skit, Cheri is interrupted by the one and only Judge Judy, who has come as an iron-fisted justice to show Cherie what it means to spit fire in the courtroom. If you thought Cheri’s Judge Judy was direct, you ain’t seen nothing yet. Cherie fights for a piece of the action but, she’s simply no match for the OG.
#17: Barry Gibb
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In a recurring sketch that answers the question, “What if Barry Gibb hosted a political talk show?” Jimmy Fallon played the titular character, with Justin Timberlake as his brother Robin. Inviting politicians and newsmakers for interviews is great. But of course, what is a show starring two-thirds of the Bee Gees… without some music? Around 10 years following the sketch’s debut, the real Barry Gibb makes a surprise appearance, joining the others to sing at the end of the segment. It was certainly an exciting moment for Bee Gee fans, and we get to see Barry’s humorous side, too.
#16: Matt Damon
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Brett Kavanaugh’s Supreme Court hearing was so bizarre that it didn’t require a huge leap from fact to satire. We all saw the “SNL” material practically write itself, so the only question left was: who would play the beer-loving nominee? Matt Damon delivers a faultless performance, mirroring some of the hearing’s more peculiar moments, from Kavanaugh’s constant sniffing and weird calendars to his intense mood swings and inexplicable rage. Reportedly Damon was only brought on board the night before the sketch was set to air; still, the payoff speaks for itself. We’re almost sorry that it was only a one-off occasion.
#15: Ellie Kemper, Ed Helms, Nancy Carell, & Jenna Fischer
When Steve Carell hosted the show in 2018, he made it crystal clear that an “Office” reboot was not in the cards. But then it isn’t just fans who are disappointed by the news. Carell’s old castmates appear amongst the audience to jump on the reboot bandwagon and try to persuade him to think of the money. Arguably though, the most hilarious cameo comes from Carell’s wife — and former “SNL” cast member — Nancy and their kids, who are also keen to see the show revived. He invites his co-stars on stage and we wait with bated breath... for the announcement that never comes. Well, at least we got this mini-reunion.
#14: Leonardo DiCaprio
Riding high on his Oscar nomination, Jonah Hill is brought crashing back down to earth when the audience shows more interest in his “Wolf of Wall Street” co-star, Leonardo DiCaprio. But although Leo’s name is mentioned several times, it doesn’t seem probable that he would suddenly walk out onto the 8H stage. Making his one and only appearance on the show, the Oscar-winning actor calls Hill out for acting like a big shot. He tops off his memorable cameo by reenacting one of “Titanic’s” most iconic moments. How has “Lee” never hosted before? Quick, someone gets Lorne Michaels on the phone!
#13: Dave Chappelle, Chris Rock & Tracy Morgan
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Hosting for the first time since 1984, Eddie Murphy emerged onto the stage while the audience enthusiastically chanted his name. Naturally, such a momentous occasion couldn’t pass by without some surprise appearances, which is why we were thrilled when he was joined by comedy icons Tracy Morgan, Chris Rock, and Dave Chappelle. After some first-rate banter — including a Lizzo shout-out — these cameo comedy icons pay tribute to the comedian who paved the way for their own careers… especially Chappelle, who says he’s been following Murphy’s blueprint very closely. Joined by Keenan at the end, we get to revel in some of comedy’s finest entertainers.
#12: Arnold Schwarzenegger
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Dana Carvey and Kevin Nealon’s popular recurring skit featured Hans and Franz, two Austrian body-building enthusiasts who are more about the flex than the fitness. They idolize their “cousin” Arnold Schwarzenegger, who usually appears in the form of a cardboard cutout in the background. However, the real Schwarzenegger joined the show for a surprise cameo, too. In one skit, he invites the pair to give a fitness pep talk to some kids but, it soon becomes apparent that they’re simply clueless. Not only does he take the wind out of their sails, but he also shows them how it’s done.
#11: Bryan Cranston
After the 2016 election, it often felt like reality was imitating fiction. That’s why it seemed rather fitting that “SNL” would turn to fictional TV to send up some of the unusual choices who were joining the new cabinet. Walter White is brought out of retirement to become the new head of the DEA, upon Steve Bannon’s recommendation. He explains how his credentials are really no different than those of his new colleagues, even faking his own death. The skit is peppered with plenty of hilarious “Breaking Bad” references, and his countless witty quips have us cracking up every single time.
#10: The Five-Timers Club
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When Justin Timberlake made it to the "five-timers club" of celebrities who've hosted "SNL" 5 times or more, the show resurrected an occasionally recurring skit that pictures the club as an actual club, of the members-only variety. This time, the show pulled out all the stops and featured cameos from no less than 8 people: Paul Simon, Steve Martin, Chevy Chase, Martin Short, Dan Aykroyd, Alec Baldwin, Candice Bergen, and Tom Hanks all make appearances. The bit about the club members entertaining themselves by forcing current "SNL" players to fight each other to the death is a particularly funny one.
#9: Sarah Palin
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This cold open featuring Tina Fey's popular Sarah Palin impression starts innocently, with Fey, as Palin, taking questions from the press and giving typically silly answers. But then it cuts to a cameo montage of people criticizing Lorne Michaels for leading with the bit, including Mark Wahlberg, Alec Baldwin, and finally Sarah Palin herself. Fey is eventually notified that the actual Sarah Palin will be taking the stage, and bows out so that Palin herself can kick things off. It's a quick, tight bit with an unexpected twist, much like the time Hillary Clinton visited Kate McKinnon.
#8: Paul McCartney
Two of “Saturday Night Live”’s most popular hosts - Steve Martin and Alec Baldwin, who have hosted the show a combined total of more than 30 times to date - waggle their egos at each other in this 2006 skit, each trying to prove that theirs has been the more illustrious hosting career of the two. Seeing the two hosts together is entertaining enough – and seeing Martin Short as a waiter only adds to the fun – but it's Paul McCartney's wordless appearance that really steals the show. Not even Steve Martin's quick joke (“It's Paul Simon!”) can hide both actors' genuine surprise at seeing Sir Paul up close and personal.
#7: Larry David
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Back in 2015, “SNL” decided to send up the Democratic presidential primary candidates with a couple of special guest impressions. Although this cold open also featured Alec Baldwin as Virginia Senator Jim Webb, Larry David stole the show with his cantankerous, scowling Bernie Sanders impression. His spot-on cameo appearance as the famous U.S. Senator was such a big hit with audiences that the “Curb Your Enthusiasm” comedian has revisited it several times since then, and even appeared alongside the actual Bernie Sanders in a later sketch. For "SNL" viewers, it came as no big surprise when the two later found out they are related by blood.
#6: Alex Trebek
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Will Ferrell's mega-popular skits featured the future “Elf” actor as a worn-out, frustrated version of “Jeopardy!” game show host Alex Trebek, with three clueless celebrities – played by cast members and guests – taking the podium to answer simple pieces of trivia in the form of a question. Darrell Hammond's foul-mouthed Sean Connery impression is the first thing most people remember about it, but the last of the regular "Celebrity Jeopardy!" segments also featured a surprise cameo from the real Alex Trebek himself. He came out to help send off Ferrell from the segment... and let Hammond's Connery get in a few more off-color jabs at both their expense.
#5: Alec Baldwin
Ever since the first televised debate of the 2016 U.S. Presidential election, “SNL” has been relying on surprise appearances from perennial host and guest star Alec Baldwin to do comedic justice to the resort mogul's over-the-top personality and distinctive speech patterns. At times, Trump can seem like an impossible man to parody, but Baldwin always delivers the goods, walking a fine line between the real President's outrageous actions and the winking zaniness of a great “SNL” parody. No matter how many times he reprises the role, we never get tired of watching this master Trump satirist at work, especially whenever he shares the screen with Melissa McCarthy as Sean Spicer.
#4: Madonna
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Musical guest Lady Gaga showed off her sketch comedy chops in this classic segment, which sees the singer joined on the stage by pop megastar and “SNL” favorite Madonna, in a surprise cameo appearance. The two play vicious and self-absorbed versions of themselves, trading venomous insults with each other as they try, and fail, to get along and perform together for the “Deep House Dish” music program. The skit packs in a flurry of subtle references to both singers, and pop music fame in general. Years later, the two stars actually would have a public disagreement, but that feud never reached the laugh-out-loud heights of this 2009 gem.
#3: Barack Obama
Back in 2007, when Barack Obama was still just a primary candidate for the office of President of the United States, he made this typically deadpan cameo on a skit set at Bill & Hillary Clinton's Halloween party. Various political guests show up in costume and share a joke or two with the beleaguered hosts; finally, a tall, slim guest approaches in an Obama novelty mask. After the usual commentary from the Clintons, their guest removes the mask to reveal... Senator Obama himself. It's a great example of the dry sense of humor Americans came to expect from Number 44 in the subsequent years of his presidency.
#2: Robert De Niro & Joe Pesci
Jim Breuer's recurring "The Joe Pesci Show" sketch featured an impression of the famous actor as a violent maniac, similar to his characters in the films "GoodFellas" and "Casino," who used any perceived slight from his guests as an excuse to assault them. The segment also often used special guests to play Robert De Niro, who would validate Pesci's anger and join in alongside him. So when the real Pesci and De Niro eventually showed up on the sketch in an unannounced double cameo, the comedic tension was almost too much. The two veteran actors played their parodied selves to a “T,” and brought the house down in the process. Before we unveil our top pick, here are a few honorable mentions. John Goodman His Linda Tripp Impression Is Comedy Gold Jake Gyllenhaal Gyllenhaal Releases His Inner Elphaba as the Guy Who Travels in Pajamas John Mulaney “SNL” Alum Joins Buddy Pete Davidson on “Weekend Update”
#1: Barbra Streisand & Madonna
“SNL”’s studio audience was already delighted enough by the surprise appearance of superstar pop singer Madonna on this episode of Mike Myers' recurring talk show sketch, but even the Material Girl was star-struck when the legendary Barbra Streisand popped in. She entered at just the right time, too, during a moment when both characters were praising her singing voice. The rare cameo by Streisand was the result of a last-minute, off-the-cuff arrangement with “SNL” head honcho Lorne Michaels, so none of the cast knew it was happening until it did. The surprise and admiration radiating from Madonna's face was unscripted, totally real, and impossible to forget.
