#17. B.o.B. "Autotune" (2008)
Although this isn't a real song, but a parody about the overuse of Auto-Tune in hip-hop, it's still great. Even if it's meant to suck, we're so past irony (as in, a rapper who can and does sing fairly well using a pitch correction program to make himself sound bad but still sounding better than a lot of other people who seriously tried to use said program) that we're just impressed at how funny the video actually turned out. Because seriously, if Chappelle's Show had still existed, we suspect this is the exact kind of skit Dave would have made.