Though his comedy group The Lonely Island (also made up of Jorma Taccone and Akiva Schaffer) may still contribute Digital Shorts, this is the end of their regular involvement with the show. It’s too bad, as the faux hip-hop trio have contributed quite a few highly catchy (and incredibly funny) tunes over the years, and doubled up on the star power by having a pop star jump on board. Jump below for our 10 favorite musical Digital Shorts featuring pop stars to air during Samberg’s seven year stint on SNL. Don’t agree with our picks? Then throw this list on the grrrooooooound!
#10. “Jack Sparrow” Feat. Michael Bolton
Michael Bolton becomes cool again, and all he had to do was dress up like a pirate.
#9. “Creep” Feat. Nicki Minaj
It’s a weird one, but it’s still better than most of the tracks on Roman Reloaded.
#8. “100th Digital Short” Feat. Justin Bieber
Bieber doesn’t seem too pleased with the way the short turned out, but we’ll never be able to stop laughing at Jon Hamm-as-Sergio grinding up against The Bieb.
#7. “Iran So Far” Feat. Adam Levine
One of the group’s sweeter love songs. Even if it happens to be about Iranian President Mahmoud Ahmadinejad.
#6. “Motherlover” Feat. Justin Timberlake
This song is so good, we only wish we could really sing it to our moms without them looking at us funny.
#5. “Shy Ronnie” Feat. Rihanna
Shy Ronnie is hilarious no matter where he pops up.
#4. “3 Way (The Golden Rule)” Feat. Lady Gaga & Justin Timberlake
The usually so-serious pop star shows some levity as the lady standing between Samberg and Timberlake’s loins.
#3. “I Just Had Sex” Feat. Akon
And it felt so good.
#2. “Dick In A Box” Feat. Justin Timberlake
We think we prefer “Motherlover” as the better song, but JT’s first collaboration with The Lonely Island crew is just too classic. He even performed it live with Samberg during his Madison Square Garden concert!
#1. “I’m On A Boat” Feat. T-Pain
This song was not only awesome enough to get nominated for a Grammy, it got a shout-out by Miley Cyrus at the 2009 MTV Movie Awards. It’s such a delicious proclamation, people just want to shout it out even when they are not currently on a watercraft.
HONORABLE NON-POP-STAR-FEATURING MENTIONS: “Natalie’s Rap”, “Jizz In My Pants” and, of course, “Lazy Sunday” never get skipped over when they pop up on our iTunes.
What’s your favorite song by The Lonely Island? Share them in the comments!