The Top-10 Lonely Island Songs

For those of you who somehow don’t know, The Lonely Island is a comedy troupe most famous for their music. Their members: Andy Samberg, Akiva Schaffer and Jorma Taccone have appeared in numerous films and shows but, to me, their music is what really sets them apart.

To date, they have released two albums (Incredibad, Turtlekneck & Chain) with songs featuring major recording artists Akon, T-Pain, Michael Bolton, Nicki Minaj, Rihanna, Lady Gaga and Justin Timberlake. It’s tough to narrow order this list, but here is my attempt.

10. Threw it on the GroundSamberg

This is a song unknown to most, even fans of Lonely Island. It isn’t exactly a sing-along piece or even something to listen to on your iPod, but watching the video makes it completely worthwhile. Just watch if you haven’t yet and you can enjoy seeing Andy enjoy breaking things.

9. MotherloverSamberg and Timberlake

This song is hard to talk about without getting graphic. Basically it starts off after Samberg and Timberlake are released from jail and need to come up with a Mothers Day gift for the most important women in their lives. What takes place… well just watch and see if you don’t already know.

8. Ji** in my PantsSamberg and Taccone

The first time I heard this song I was very confused as to what was going on. I didn’t realize it was Lonely Island until 30 seconds into the song and didn’t like it until I re-watched it with that in mind. This is probably the second most catchy song they have and it has some great lines and a fantastic cameo by Jamie-Lynn Sigler. Samberg’s face after he watches the end of The Sixth Sense is seriously one of the funniest things I have ever seen.

7. Like a BossSamberg

A lot of people will say I’m wrong for including this song on the list, let alone this high, but I personally enjoy Samberg telling Seth Rogen about his typical day of work. The cameos are solid in this piece, and all I can say is I wish I could work at his office.

6. The Golden RuleSamberg, Timberlake and Lady Gaga

This is the third song by Timberlake and Samberg (and second on this list) featuring their two characters and their journey through life. In this particular ballad these two have the misfortune of realizing the women they have both been seeing is actually just one woman. Upon this realization they must decide whether to continue on the journey together. What you end up learning is that the Golden Rule “dates back to Ancient Greece, talkin’ ’bout Caesar.”

5. Lazy SundaySamberg and Chris Parnell

This is, if my information is correct, the first widely released song by the group. As one of the first Saturday Night Live ‘Digital Shorts’, it caught on like wildfire. I remember you couldn’t go anywhere without hearing someone say they were “Ghost like Swayze” or yelling “The Chronic-what-cles of Narnia!” This was the biggest thing since Rick James and helped propel these guys to a ton of success. If for no other reason, that’s why it deserves being on the list.

4. Jack SparrowSamberg, Schaffer, Taccone and Bolton

This is another song I wasn’t 100% sold on at first, but now I am addicted (and to be completely fair, my uneasiness may stem from the Michael Bolton reference in Office Space). I don’t really know if it’s possible to give a couple word synopsis, but basically the group is trying to record a song with Bolton who can’t help but sing about Pirates of the Caribbean. The music is certainly the best part of the song, but seeing Bolton dress up as Captain Jack Sparrow and sing about the Isle of Tortuga is amazing.

3. Di** in a BoxSamberg and Timberlake

One of the earliest hits for the group, and the first of the three with Timberlake on this list, was Dick in a Box. It’s a song which was able to gain fame due to its release as an SNL Digital Short. When I first heard it, I was honestly not a huge fan, but after giving it another chance I found myself quoting it at the most inappropriate times. In the song, Samberg and Timberlake have found the best gifts for their ladies and go on to talk about how to make it and all the best times to give it.

2. I Just Had SexSamberg, Taccone and Akon

This is definitely the groups most catchy song that, if not for the lyrics, you would love pumping through your speakers while driving around town with the windows down. Just like with I’m on a Boat, the theme is simple: these men (minus Akon) have just had sex and want to talk about how great an experience it is. The first time I saw Samberg say “honestly I’d have sex with a pile of manure/ With that in mind the soft, nice-smellin’ girl’s better,” I lost it and I still love the line. Also, the fact that this song features Blake Lively and Jessica Alba as the women Samberg and Taccone bed is a huge plus.

1. I’m on a Boat: Samberg, Schaffer and T-Pain

This was the song that really put the group on the map. I remember all of the clubs at college and on Spring Break played this every night. The song itself is a simple theme, three guys who are on a boat which is clearly superior to land. T-Pain’s autotone and lines like “I never thought I’d be on a boat, a big blue watery road,” along with his hand gestures get me every time. This was the first team that I can recall Schaffer was one of the leads on a song and he did not disappoint while he was “on a dolphin doin’ flips and sh**.”

Making this list was great because it gave me yet another reason to watch all these videos again. If you think something was ranked poorly or even if I missed a song, let me know below.

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