Anthony “Top Dawg” Tiffith, an imposing figure at 6 foot 1, tends to wear a stern look under his signature red baseball cap. It’s a face sculpted on the streets of Watts, Los Angeles, during the drug-infested ’70s, ’80s and ’90s. But on this September afternoon, climbing a set of stairs to the lounge of a Hollywood studio, the 47-year-old founder/CEO of Top Dawg Entertainment, known to his friends as Top, is in a jovial mood. He just spent a few private moments trading jokes with TDE’s co-president, Dave Free, that left the two doubled over with laughter. And after that, in between stone-faced poses for cameras, he was cracking up with Kendrick Lamar, TDE’s MVP -- or, as some would argue, simply the greatest rapper alive.
Lamar’s in a fine mood, too, as he follows Tiffith up the stairs. You’d never know from his calm, coiled energy that only four days before he wrapped his 36-date North American tour, DAMN. (And, less than a week before that, put on a riveting, pyrotechnics-filled performance that opened the MTV Video Music Awards.) It’s Tiffith who takes the seat at the head of the conference table -- Lamar, 30, sits to his left -- and starts the conversation off by smiling and saying, “I’m on the cover, so I decided I’ll speak a little bit. Not a lot, just a little bit. I like to stay behind the scenes and let my artists do their thing.”