The 10 Best Lonely Island Videos Of All Time

Photo: Mark Davis/Getty Images.
The Lonely Island started out as three longtime best friends crafting silly parody raps. Now, the comedy trio — Andy Samberg, Jorma Taccone, and Akiva Schaffer — is releasing its first original feature film, Popstar: Never Stop Stopping. (They directed, starred in, and co-wrote 2007's Hot Rod using an original screenplay drafted by Pam Brady.) In-between, the boys have produced a hilarious and sizable body of work, including three studio albums and dozens of viral videos.
We first met the Lonely Island on Saturday Night Live in 2005. They wrote live skits and started SNL Digital Shorts — writing, directing, and starring in music videos with outrageous lyrics and viral appeal. (At one point, we all knew the words to "Dick In A Box.") The shorts feature singers like Michael Bolton and Rihanna, as well as actors like Blake Lively and Tom Hanks. Though The Lonely Island has had a lot of hits, there have been a couple of misses, too (ahem, Hot Rod). We pared down The Lonely Island's catalogue down to its 10 best videos.
1 of 10
"Lazy Sunday" (2005)

An early gem. The trio's second SNL sketch ever became a viral sensation overnight. It follows their Sunday matinee adventures to see The Chronicles of Narnia in theaters.
2 of 10
"Dick In A Box" feat. Justin Timberlake (2006)

This R. Kelly sex-song knockoff is about giving your lover your penis dressed up as a holiday present. Kristen Wiig and Maya Rudolph star as the, um, lucky ladies, and JT knocks it out of the park. Would you believe us if we told you this snagged an Emmy?
3 of 10
"Natalie's Rap" feat. Natalie Portman (2006)

Natalie goes gangster in her rap debut. Here, she pretends to shed her good-girl image. We have to hand it to Portman on this one — she did an incredible job with gross (but amazing) lines like, "All the kids looking up to me can suck my dick," and, "I bust in dudes' mouths like gushers, motherfucker." Lovely.
4 of 10
"Ras Trent" (2008)

This one skewers the stereotypical white college kid (played by Samberg) that appropriates Rastafarian culture — accent, dreads, clothes, and all. The over-the-top offensive stereotyping is entertaining, but gets a valid point across, too. Sample lyrics: "Excuse I for my skanking / Give thanks and praise / Me toil part-time / At jah Cold Stone Creamery."
5 of 10
"Jizz In My Pants" (2008)

This single from The Lonely Island's debut album, Incredibad, is about early ejacluatlion, of course. It's crude, lewd, and disturbingly easy to get stuck in your head. Each verse gets sillier: "When Bruce Willis was dead at the end of Sixth Sense I JIZZED IN MY PANTS / I just ate a grape and I JIZZED IN MY PANTS."
6 of 10
"Like A Boss" feat. Seth Rogen (2009)

Rogen conducts the best job interview, ever, and Samberg raps about being a boss (but not really). I'll let the lyrics do the talking:
"Hit on Deborah (like a boss) / Get rejected (like a boss) / Swallow sadness (like a boss) / Send some faxes (like a boss) / Call a sex line (like a boss) / Cry deeply (like a boss) / Demand a refund (like a boss) / Eat a bagel (like a boss)."
7 of 10
"I'm On A Boat" feat. T-Pain (2009)

The most epic celebration of yachts, nautical luxury, and Titanic. Every time a teenaged boy stepped onto an aquatic vehicle of any kind in 2009, he was essentially obligated to belt out the obnoxious chorus.
8 of 10
"Shy Ronnie" & "Shy Ronnie 2: Ronnie & Clyde" feat. Rihanna
(2009 & 2010)

Shy Ronnie is so nervous to perform with RiRi that he can barely muster a whisper. He wrecks a classroom sing-along in the first video and a bank robbery in the sequel, here. Rihanna is flawless and Samberg is flawless in his portrayal of a nerdy ginger fourth-grader.
9 of 10
"I Just Had Sex" feat. Akon (2010)

This celebration of boning sounds pretty much like every other Akon song, which I guess is the point. But the unsexy sexual lyrics ("It felt so good when I did it with my penis / A girl let me do it, it literally just happened") give it the Lonely-Island stamp, with cameos from a just-sexed Blake Lively and Jessica Alba.
10 of 10
"YOLO" feat. Adam Levine & Kendrick Lamar (2013)

The Lonely Island took the millennial acronym to a whole new level with the help of the Maroon 5 singer and the To Pimp A Butterfly rapper. The tune is actually pretty good and the 401(k) advice from Kendrick isn't bad, either.

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