“I love when he gets out of the studio and jumps into situations with ordinary people,” Reiff said. “He played ‘old time baseball’ on Long Island, he tried to reunite two former best friends that he met in Finland.”

“It’s as if the whole world is his roommate,” he added.

In 2004, NBC promised O’Brien that in five years he’d be hosting The Tonight Show. O’Brien indeed ascended to the post in 2009, but after seven months NBC gave the show back to Jay Leno when O’Brien declined to accept a later time slot, a move he felt would have betrayed the show’s integrity.

Reiff said the way O’Brien prioritized his staff in his NBC negotiations was completely in line with his character, just as he paid his staff out of his own pocket during the 2008 writer’s strike.

O’Brien will launch a new show on TBS in November, but not before he wraps up his “Legally Prohibited From Being Funny on Television Tour.”

“He’s a keeper—I was shocked they didn’t want to keep him and build a long-term franchise around him,” Reiff said of the NBC executives. “But the way he handled it shows his character. His audience has loved his humor for a long time, but the battle with NBC gave them a glimpse of his character. That’s why they have rallied around him the way they have.”

In his 1985 profile, O’Brien made a rather prophetic closing remark:

“The perfect world would be where the ‘Conan O’Brien Show’ would be on, and you’d be reading my short story somewhere and wearing my designer jeans,” he had said.

As far as realizing dreams goes, O’Brien has done quite nicely, though we’re still waiting on the designer duds. Maybe by his 50th reunion?

—Staff writer Julie R. Barzilay can be reached at jbarzilay13@college.harvard.edu.