5. The Legend of Zelda
At some point, a Nintendo executive decided the only way to sell their medieval fantasy adventure games was through stilted, out-of-place raps. Unfortunately, no one questioned this guy's decision-making for about 7 years, even when he demanded an extra from Revenge of the Nerds do some beatboxing while some other doofy 80's kid performed a rap that sounded like it was written on-set 5 minutes before the cameras started to roll and the kid was just starting to get the hang of reading cue cards.
Given Nintendo was attempting to "be cool" by including this insanely uncool rap, whatever thin veil of radical-ness they thought they had built for themselves utterly collapses when the commercial ends with a reminder that your mommy and daddy can set up the NES for you.
Wikki Wikki Wick!
4. Knuckles' Theme
The Sonic franchise has a long, messy history of lacking self-awareness, generally-speaking. While occasionally Sega seems to allow itself to admit it's a silly franchise that shouldn't take itself seriously, more often than not we get Knuckles hip-hop/rap songs and Sonic being in love with a human princess. The actual music behind the song actually isn't too bad but the fact that it's a sincere song about Knuckles the Echidna turns it into something wholly ridiculous and sorta embarrassing for all parties involved. Then again, this might not even be in the top 10 embarrassing things from the Sonic franchise, so at least it has that going for it.
You can call me Knuckles, unlike Sonic I don't chuckleI'd rather flex my muscles.
3. Fugitive Hunter
This song may just be the reason terrorism exists in the world.
Fugitizing, captivizing where's Abudulah, he's been hidingHijacking, straight surprises flyin down blowin up high risesFive hundred soldiers in disguises