10. Shy Ronnie
The digital-short gags work best when they are straight-up genre parodies. Plenty of that coming, but Shy Ronnie doesn't quite get there. The weight of the joke is instead passed to a hopelessly meek MC and making Rihanna's speaking voice an auto-tuned melody. It has its moments, but it gets a lot better.
9. Iran So Far
This is the digital-short wheelhouse: Take a Top 40 genre and re-create it exactly on some ludicrous subject. Here it's the soft-rock ballad on the subject of a totalitarian world leader. Adam Levine does the sad-eye thing as well as he does in his usual shtick. Negative points for the semi-current-affairs hook -- the best exist in their own self-contained worlds.
8. The Creep
There's a lot to love here: The John Waters cameo, the awesome sight gags of the three Lonely Island dudes creeping up on alarmed women. And Nicki Minaj is such a natural fit -- she's been playing convincing characters all along in her music. But it doesn't feel as natural as the best on this list.
7. Mother Lovers
Our favorite tacky-suit-wearing '70s crooners reprise their "Dick in a Box" roles, this time in the service of fucking each other's mothers. Justin Timberlake obviously loves doing this sort of thing (parody videos, not fucking his friend's mother), and Lonely Island has never found a stronger musician collaborator. This one, while not quite as good as the original, is still pretty great.
6. I Just Had Sex
It's all killer from here on in. Akon does Akon, and the beauty here is in reduction: It's basically just a lover-man anthem except, you know, really frank and specific. Bonus points for sporting cameos from Blake Lively and Jessica Alba.
5. Lazy Sunday
The first great digital short has held up remarkably well. No big-name guest stars, no production value, but Andy Samberg and Chris Parnell don't need it. Gangsta rap on the subjects of shitty kids' movies, cupcakes and Google maps. Still awesome.
4. Dick in a Box
The most famous digital short is still great, but it's actually aged pretty poorly. Part of the problem is that the novelty factor is gone: How many shitty Dick in a Box jokes have you seen done by dudes who don't get the irony? Still, as previously stated, Justin Timberlake is unbelievable in these things.
3. Natalie Raps
This would have been great even without the exaggerated docile interview interspersed with presumed gentle-lady Natalie Portman just roughing shit up. This one works because Portman manages to be truly threatening throughout -- all 5'3" of her. It's always amusing when celebrities play against type. And you have to remember that this was just slightly before everyone got smart and started making fun of themselves on the Internet.
2. Boombox
The best actual song on the list, Boombox also benefits from simplicity. Committed all the way through, Julian Casablancas will probably never again deign to appear from behind his meticulously constructed wall of New York cool. Fingerless gloves all day long, people.
1. I'm on a Boat
You've already seen it, but there's a reason for that. The one song on this list that actually managed to kill a musical style -- it just sounded too perfectly like the real thing. Gonna guess T-Pain is seeing diminishing returns on this appearance these days. Also: By far the best celebrity introduction in any digital short.