Musician and actor Justin Timberlake has shown up on Saturday Night Live so many times that he's almost become an unofficial cast member. He's also so relaxed and funny and fits so seamlessly into the show that you'd swear Timberlake was an experienced comedian himself -- or, at the very least, has a comedy background. Instead, his background is The Mickey Mouse Club. Check out this list of the eight best sketches from Timberlake's many appearances on the show.
Probably the most popular Justin Timberlake sketch of all time, "Dick in a Box" helped launch the Digital Shorts created by Andy Samberg and The Lonely Island for Saturday Night Live. A parody of early-'90s R&B ballads and a new holiday classic all rolled into one, "Dick" quickly skyrocketed from SNL sketch to cultural phenomenon -- it gave the show some well-deserved heat and gave Timberlake a lifetime pass as a host. The sketch was that memorable.
2. "Hip Hop Kids" (12/16/06)
From the same show as "Dick in a Box" comes this forgotten gem, which was buried late in the episode but was an incredibly funny standout that never got its due respect. Timberlake stars (alongside Amy Poehler, Maya Rudolph, Kenan Thompson and Jason Sudekis) as the host of a dancing kids' show whose cast has been trapped in a mine. That concept is funny enough, but the sketch gradually gets better as the kids have to contend with dangerous falling rocks and ravenous cave creatures. It's absurd and hilarious, and Timberlake actually manages to outshine the rest of the regular cast members.
Timberlake and Andy Samberg tried to recapture their "Dick in a Box" lighting a second time and pretty much succeeded. In this Mother's Day-themed Digital Short, the pair reprise their R&B singer roles in a jam about sleeping with each other's moms (played by Susan Sarandon and Patricia Clarkson). I still contend that it might have been funnier if the moms were women that not everyone wanted to sleep with, but whatever; at this point, Timberlake and Samberg are two for two.
4. "Breakfast Competition" (10/11/03)
This was the first -- and possibly the best -- of Timberlake's recurring "Bring it on down to..." sketches. The premise is always the same: two guys in funny suits, each shilling for something on the street. Timberlake is the consummate one-upper -- his costumes are better, his dance moves are cooler and his energy is much more infectious. Just the site of Timberlake in a giant foam omelet is funny, but what takes the sketch over the top is how hard he sells the whole act. It's a great example of a sketch that would have been forgotten in the hands of some other host, but Timberlake makes it a standout. There's a reason it's been repeated so many times.
JT stopped by this Paul Rudd-hosted episode to pop up in a few sketches (including one heavily-talked about sketch with Beyonce, discussed further down the list). But this brief segment he did on "Weekend Update" was possibly the show highlight, as Timberlake ran through exactly what a show hosted by him would look like in two minutes. The funniest part about it is that it's absolutely accurate -- as his hosting gig later in the season would pretty much confirm.
In this too-often-repeated sketch, Timberlake plays ex-Bee Gee Robin Gibb, co-host of "The Barry Gibb Talk Show" (Barry is played by former cast member Jimmy Fallon). The characters that Timberlake and Fallon play and the affectations they've hit upon for their voices are usually funnier than any of the content in the sketches; plus, the two always seem to having a good time together. I dare you to try and get that theme song ("Talkin' it up...on the Barry Gibb Talk Show...") out of your head.
7. "Single Ladies" (11/15/08)
Timberlake wasn't the host of this episode from November, 2008 (it was Paul Rudd), but he managed to pop up in several memorable sketches and pretty much steal the show. The most talked-about sketch of the night was this parody of Beyonce's music video for "Single Ladies," in which Timberlake, Bobby Moynihan and Andy Samberg played the parts of backup dancers fully decked out in leotards and high heels. It's pretty much a one-joke premise and the guys are pretty shameless in their mugging for laughs, but you once again have to appreciate Timberlake's willingness to demolish his ego for a joke -- particularly when he was just showing up as a goof.
Though most of Justin Timberlake's best SNL are the ones that play games with his ego, "Immigrant Tale" is mostly about how awesome he is. An ancestor of Timberlake arrives to the U.S. and speculates what kind of life the future Justin will have (including one pretty tasteless confession to sleeping with Britney Spears). What's funny about the sketch -- aside from Timberlake's performance -- is how outlandish all of the predictions sound in that context, until you realize that they've all come true.