One of the most underrated and overlooked eras of hip-hop was the Rapper + Dorky White Guy period of the mid 2000’s. People forget, but it was a thing for singer-songwriters to collaborate with hardcore rappers. The former personify the “misunderstood I’m probably from an affluent background but I’m paying a lot of money to look like a bum” archetype. This is a stark contrast to the flashy, bombastic rap personalities they collaborated with. Let’s never forget Birdman wore a Rolex on each wrist in the “Bling Bling” video.
The best collabs after the jump.