Wale is learning not to make a big deal about nothing. The Washington, D.C., rapper rose to fame off of street singles like "Nike Boots," followed by a slew of hit singles, including "That Way," "Lotus Flower Bomb," and "Bad." Despite his successes, Wale's always had a chip on his shoulder, quick to take issue with anyone who doubts his status as one of the best in the game—like the time he called the Complex offices to voice his displeasure with being left off of our Best Albums of 2013 list. But through it all, he's always had a soft spot for the comedy of a certain white, Jewish comedian. In 2008, Wale released The Mixtape About Nothing, a rap album heavy on Seinfeld references, including a cameo from Julia Louis-Dreyfus, a.k.a. Elaine Benes. Later that same year, Wale met Jerry Seinfeld himself, and the two became fast friends.

This year, the pals collaborated on Wale's upcoming project, The Album About Nothing. Unlike Wale, Seinfeld learned long ago to let things roll off his back. Jerry doesn't much care what people say on Twitter. Nor does he care much about lists. Sit the two of them down together and what you get is a hilarious master class in celebrity. For the first of Complex's three December/January cover stories, we sent Joe La Puma, director of content strategy, to chop it up with the odd couple at NYC's Remedy Diner, while photographer Chris Buck captured it all for posterity. Expect the unexpected.