With loads of winning sketches and classic SNL Digital Shorts like “Lazy Sunday”, “D*** in a Box”, and a star-studded list of hosts, NBC’s Saturday Night Live had a great run in the 2000s. SNL has a proud tradition of celebrity appearances and cameos that enhance the comedy and bring crowd-pleasing power to the show.
These appearances are also a reminder that famous people don’t always take themselves too seriously, which can be quite refreshing to watch. And the list of celebrity cameos for the 2000s was full of recognizable stars who pitched in for some very funny viewing. So, here’s a ranking of the ten best celebrity cameos for that decade.
10 Dave Matthews (Joseph Gordon-Levitt & The Dave Matthews Band, 2009)
One rock star portrays another in this spaced-out sketch. Specifically, mellow rocker, Dave Matthews, steps in to do a convincing portrayal of a drug-addled Ozzy Osbourne. Dave’s best lines include classics like, “You can’t fly a bicycle” and “I’m not an octopus having a cr*p in the back of a van!”
He also gives a solid performance of an updated version of Black Sabbath’s “Iron Man”, with lyrics that reflect Ozzy’s more sedentary lifestyle. The song is renamed, “I Am Tired, Man”, and it waxes lyrical about taking it easy while wearing sweatpants. The parody was very relevant at the time, with the recent success of reality show, The Osbournes, featuring a sweatpants-wearing Ozzy as the basis for this surprisingly accurate Dave Matthews parody.
9 Matt Damon (Gwyneth Paltrow & Ryan Adams, 2001)
Besides Gwyneth Paltrow and Chris Kattan doing a great Grease musical parody, Matt Damon steals the show with his cameo as a caricature of himself, when he takes Chris Kattan’s Mango on for blowing too hot and cold and slaps Mango cheekily on the butt.
A quick, witty Ben Affleck reference later, and he exits the room. It’s a very speedy in-and-out appearance, but it ties the sketch together perfectly, and the audience was clearly taken aback when Damon arrived. A good surprise celebrity appearance like this one always makes for a memorable SNL moment.
8 Mike Tyson (James Franco & Muse, 2009)
Appearing in the “What Up With That” sketch next to an unlikely co-star — Jack Briar of 30 Rock fame — the notoriously tough ex-heavyweight champ looks quite uncomfortable throughout, as Kenan Thompson’s glory-hound host, Diondre Kole, sings over Tyson while he tries to get a word in edgeways, to promote a documentary about his life.
James Franco and Kristen Wiig join in as a pair of over-the-top performers as Tyson gets progressively more annoyed until finally, he gives up and joins in, adding a spectacularly silly dance of his own to the mix. The overall silliness of this sketch is enhanced by Tyson’s willingness to make fun of himself and it’s great fun to watch.
7 Robert De Niro (Dana Carvey & The Wallflowers, 2001)
After a scathing review of Meet the Parents by Weekend Update host, Jimmy Fallon, Robert De Niro joins Jimmy and Tina Fey on the Weekend Update to take Jimmy on about his Robert De Niro impression.
Two minutes of the awkwardness then ensues with Jimmy Fallon pushing back his own bashfulness and laughter to argue with the Taxi Driver star about his own De Niro impression. De Niro insists that “He doesn’t do that” and ends off the sketch with his own whiny Jimmy Fallon impression. Fallon looks really surprised, but does manage to hold it together somehow.
6 Sarah Palin, Tina Fey, Mark Wahlberg and Alec Baldwin (Josh Brolin & Adele, 2008)
With Josh Brolin hosting and Adele performing, and a guest appearance by Oliver Stone, this one was a bumper show. Tina Fey had been doing a recurring parody of Alaska’s Governer and Vice Presidential hopeful Sarah Palin on SNL for a while. And this episode’s cold opening is a Fey/Palin press conference, where Tina Fey hams it up as the Governer, as usual.
Backstage, the real Sarah Palin and Lorne Michaels observe, as Palin makes a scathing comment or two. Mark Wahlberg pops in, looking for Andy Samberg so he can bash his head in, and Alec Baldwin swings by to make things even more awkward with Palin. When the real Sarah Palin makes her entrance, Tina Fey sheepishly walks off the stage.
5 Sacha Baron Cohen (Hugh Laurie & Beck, 2006)
Just before the release of the movie, Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan, Sacha Baron Cohen joined Lorne Michaels in an SNL cold opening. It starts with Michaels, citing budget cuts as he sips expensive whisky poured from a crystal decanter, and confessing that a foreign government has bought an SNL segment.
Enter Borat (Sacha Baron Cohen), representative of the Kazakhstan Ministry of Information. In his signature style, Borat makes awkward jokes and references to outdated SNL mainstays like Coneheads and Wayne’s World. Borat’s off-color humor and suggestive comments leave the audience feeling both awkward and amused.
4 Paul McCartney, Martin Short, and Steve Martin (Alec Baldwin & Christina Aguilera, 2006)
The sketch takes place in the “Platinum Lounge” (which could also be the Five-Timers’ Club), an exclusive club for past SNL hosts, where Steve Martin and Alec Baldwin argue about who’s had the best SNL hosting career. Fellow actor and comedian, Martin Short, is also in the sketch as a humble waiter. But it’s Sir Paul McCartney who steals the show.
His appearance clearly comes as a complete surprise to both Baldwin and Martin. Baldwin is at a complete loss for words and even the quick-witted Steve Martin’s improvised response lacks its normal luster. Best of all, the ex-Beatle doesn’t even have any lines and Martin Short introduces him (as part of the joke) as Paul Simon.
3 Barack Obama (Brian Williams & Feist, 2007)
Before Barack Obama was elected President of the United States, he made an appearance in an SNL cold opening featuring Bill (Darrell Hammond) and Hillary Clinton (Amy Pohler) at The Clinton’s Halloween party. Initially, he appears as a stranger in an Obama mask, but removes it to reveal that he is actually the man himself.
He then plays it very straight, making Amy Pohler’s Hillary feel particularly irritated. Obama was later impersonated by the likes of Jay Pharoah and Fred Armisen, and there’s been a lot of talk about him potentially hosting one day, though there’s been no official news on that yet.
2 Lady Gaga and Madonna (Ryan Reynolds & Lady Gaga, 2009)
Pop icons Lady Gaga and Madonna parody themselves on this “Deep House Dish” sketch, playing opposite Kenan Thompson as DJ Dynasty Handbag and Andy Samberg as T’Shane, two unremarkable hosts on a fictional MTV late-night show that’s holding auditions for new performers.
Lady Gaga and Madonna try to outshine each other on stage, arguing in song about who’s a better hitmaker. Song soon turns into a physical altercation, and they go at each other, both verbally and physically throughout the sketch. Apparently, they did have a real-life falling out later on, though it’s doubtful that it ever turned as petty as this.
1 Justin Timberlake (All of Them)
Justin Timberlake was an SNL regular in the 2000s, appearing as host a few times and making several surprise cameo appearances. He was a major component of the SNL Digital Shorts success with hits like “D*** in a Box”, which made its debut on SNL in 2006. He subsequently featured on a few more Lonely Island offerings too. His appearance alongside Jimmy Fallon in the Barry Gibb Talkshow sketch as Robin Gibb saw him do a hilarious Bee Gees parody.
His role as the cartoon character, Irving Hillman, alongside his now-wife, Jessica Biel, is both unsettling and hysterical. And his surprise walk-on in Britney Spears’ opening monologue with Chris Kattan is hilariously awkward. Timberlake is a regular SNL player that always makes for a few great laughs.