Tom Petty & Drake
What it would be called: Tom Petty & The Heartdrakers
Anything with the word "heartbreak" in, Drake is there with the quickness. Both artists are kind of corny in their own way, but both have undeniable hits—together they could make an album full of songs that would bring rap and rock fans together in beautiful harmony. Then Tom Petty would steal Drake's girl and the band would split up.
Also, little known fact: "I Won't Back Down" is Drake's go-to karaoke song.
Related: Read Drake's journal here.