Life is good. So why is he taking on the often-thankless task of hosting Sunday's Emmys (airing 8 p.m. EDT on NBC)?
"I was under the mistaken impression that it pays well," O'Brien told The Associated Press this week. "I actually asked my producer, `Do I get paid for the Emmys?' and he laughed. So I'm just going to take some awards backstage."
In fact, O'Brien reaped a wealth of critical praise and audience goodwill when he hosted his first Emmys in 2002. It was so much fun, he said, he was glad to be asked back for the chance to work different muscles than he does on his nightly show in New York.
"I've been in Studio 6A with the same desk and the microphone — and having lots of adventures — but you're still in that space. And when I get a chance to go into prime time and be part of a show like this, I really do feel like a kid in a candy store."
Viewers are likely to see pre-taped skits like the ones that O'Brien used effectively four years ago and stage-to-star exchanges with those seated in the Shrine Auditorium. In 2002, he feigned lust for Jennifer Aniston and drew scowls from her then-husband, Brad Pitt.
"I think it's clear I was responsible for whatever troubles they had in their relationship," O'Brien told reporters in July. "I'd like to apologize to the press and to them."
The redheaded comedian (whose uncanny resemblance to Finnish presidential candidate Tarja Halonen led O'Brien to conduct a hilarious mock campaign for her) has more to worry about than Hollywood marital strife.
A revamped nominations process was lambasted after popular and critically lauded shows like "Lost" and actors including Hugh Laurie of "House" and Edie Falco of "The Sopranos" were left out, while Lisa Kudrow of the short-lived "The Comeback" made the cut.
And because of NBC's upcoming Sunday football schedule the awards were bumped from their traditional September airing to the time of year when the fewest Americans are watching TV.
"Maybe some people will bring portable televisions when they go camping," O'Brien said. "Camping isn't camping unless you're watching an awards show. And I'm trying to see if I can get the Emmys broadcast onto the interior wall of the Grand Canyon. That would be an artistic statement and a huge ratings boost."
He knows he'll be expected to incorporate some of the nominations controversy into his remarks. (O'Brien should have no complaint: his show is up for best variety, music or comedy series.)
"These things are always walking the line. I think there are a lot of people nominated in that room who deserve to be nominated. ... The controversy is more that some people are left out," he said. "There shouldn't be just five nominees. There's too much television these days."
So how many should there be?
"Nineteen nominees. They should double the number of categories, the awards should take place over a two-week period like the Olympics and people all over the world should participate.
"And the long jump should be incorporated."