“As a comedian, you’re kind of trained to avoid authority,” says Oliver, photographed March 15 atop CBS Broadcast Center in New York. “So to suddenly be the authority is a very, very bizarre situation.”
Styling by Kaela Wohl; Oliver wears a Burberry suit, shirt and tie.
Oliver continues to seek out difficult challenges with a high chance of failure. When he's working out his material for stand-up specials, he tends to pick hard rooms like the Pittsburgh Improv. "With friendly audiences, you can kind of get by on goodwill," he explains. "But it's hard to ascertain sometimes where the gaps are. So the Pittsburgh Improv has been very useful. I love it because they'll give you no momentum."
"Obviously, look, my preference would have been that I have him forever," admits Jon Stewart. "But I also know that's not how it works here. We get these really talented people for a certain time until other people recognize that and go, 'Hey, why don't I pay him more and let him do it over here?' "
Oliver's approach is to look past the inviting tabloid fodder that constantly presents itself (hello, Anthony Weiner) and search out the sad, perplexing or troubling story and turn it into comedy that illuminates. The Trayvon Martin verdict, which came down a month into Oliver's tenure at the helm of The Daily Show last summer, is an example. "That was not easy," he admits. "You start with these feelings of disgust and rage, and as the day goes on, you kind of get excited about, 'Oh, I think we're managing to say the complicated things we're wanting to say.' "
"There’s something about living here that is inherently ridiculous because it costs too much, it’s not clean … 8 million people have made a bad choice. And I’m one of those 8 million," says Oliver.
“He made it very much his own, very quickly. I hate to say it, I missed him when Jon came back,” says HBO’s Michael Lombardo of Oliver filling in for Stewart last summer.
Growing up in Bedford, England — one of the formerly proud industrial towns north of London — the eldest of four children of schoolteachers, Oliver attended what he describes as a "rough" high school. "I grew up watching my parents deal with the consequences of what the Thatcher government did to public education in England," says Oliver. "I think it's hard to be apathetic when you're raised under Margaret Thatcher; you're going to get pushed one way or the other."