James Wolk is a very handsome man. Whether he's an odd fellow on "Mad Men" or a playboy on "The Crazy Ones," Wolk pretty much always looks good. But his TV look pales in comparison to the actor wearing a collection of multi-colored suits in the February edition of GQ.
Mystery Mad Man
When James Wolk was first cast on Mad Men, he was just as much in the dark about his character as we were. To the best of his knowledge, he would be yet another memorably charming but forgettable everyman in the backdrop. And then Matt Weiner decreed it: He shall be called Bob Benson, and things shall get weird. "The creators just kept telling me Bob was someone who felt comfortable—who always felt comfortable," Wolk says. Comfortable wearing seriously short shorts (a habit his ad-sales character on CBS's The Crazy Ones shares). Comfortable propositioning his boss with a stray knee brush....
Benson, the most interesting addition to Mad Men since Teenage Glen, was slippery and disorienting: pleasingly bland with the suggestion of danger. Like Canada if it had nuclear weapons. Wolk's Benson made viewers uneasy all season, launching absurd fan theories involving obscure Freudian conditions and time travel. The new season (premiering this spring) promises to deliver that same discomfort while making Wolk even more recognizable.
As it happens, Mad Men and this GQ spread aren't Wolk's first forays into stylish territory—he has his own fashion pedigree. Beginning at 13, he sold women's shoes in his father's store in Michigan, a nice training ground for Wolk's (and Benson's) signature golly-gee charisma. He picked up another important Benson quality hawking heels: how to bend the truth with a sweet smile. "I learned women never want to hear they have big feet. That's no fun. So you always want to guess a size down," he explains. "Be honest, but, ellipsis."