25 best award show hosts

7. Conan O’Brien

Show: 54th Annual Primetime Emmy Awards (2002), 58th Annual Primetime Emmy Awards (2006)

Memorable Moments: Conan O’Brien hosted the Emmy Awards in two years that were interesting periods for television. Back in 2002, TV was still mostly about the procedural dramas, primetime soaps, and wildly popular sitcoms. (Friends was still on the air!) But in 2006, the TV tides shifted toward something more serialized and buzz-worthy for the watercooler. This was maybe the first modern era of “peak TV,” as everyone was still tuning into shows in droves. And being so, O’Brien’s opening monologue featured a skit that paid tribute to many shows that defined that era of television: Lost, The Office, 24, House, South Park, and Dateline.

Public Reception: Much like most hosts on this list, it’s unimaginable that viewers had anything negative to say about Conan O’Brien’s two non-consecutive hosting gigs at the Emmys. For starters, he opened the 2006 awards with a tongue-in-cheek parody that poked fun at new rules that had fan-favorite series like Lost and Desperate Housewives shut out from the nominations. Also, O’Brien maintain a sharp comedic eye, and he knew which series to honor that would be more than simple flash-in-the-pan phenomenons.

Why They’re One of the Best: Looking at his work, Conan O’Brien has a different sense of humor than most of his late-night contemporaries. And he’s also armed with a self-awareness that can set him apart from the pack. As the host of the Emmys, he used his opening monologue in the traditional sense: a pseudo stand-up set skewering Hollywood, politics, and everything in between. He told jokes about NBC’s quick trigger finger to pull the plug on a show as well as he did about the Bush administration. But that odd musical number about how TV’s taking a hit from the internet? He was way ahead of the curve with that one.