Flipper
Never having seen a Super Bowl game and honestly having tastes normally anathema to "Go Football!" people, I'd want to see Flipper perform during the halftime show because it would completely leave spectators flabbergasted. It'd be really funny. The rest of my line up would be selected just for this intention.

Yoko Ono
She would have to perform "Walking on Thin Ice". If she can't make it, the SB people could just play one of those National Geographic vinyl magazine inserts of whale sounds. I had one when I was a kid from an old issue that my mother received in the 70s. Because that high-pitched sound is pretty damn close to Yoko Ono's at times. (No hate, I think she's great).

Lenny Bruce
Of course, he'd have to be resurrected from the dead. He'd fill in my Ryan-Seacrest type spot for the half-time show. You know, the commentator/emcee function. Hey, he was legendary and ballsy and said m*therf*cker a lot. The FCC would have a ball with him.