Sometimes comedy illuminates hard truths with a pointed urgency that other means can’t quite achieve. Sometimes comedy is just funny. This series of posts is mostly about the former instances, but the latter is valuable, too.

Well before Conan O’Brien became an institution with a run a late-night talk show host that rivals in length and influence some of the undisputed greats of the form, he was a neophyte whose job seemed to be in constant jeopardy. That, my friends, was the true golden age of O’Brien’s comedy, in large part because that precarious position clearly inspired him and his writers’ room filled with other scruffy upstarts to feel free to fill national broadcast network airtime with any goofball idea that amused them, no matter how slender it might be. To his credit, O’Brien maintained much of that freewheeling quality right to the end, but it had an extra hangdog charm back in the day.

For a long time, I would’ve identified this remote segment, featuring Andy Richter wandering a Grammy Awards afterparty, as my favorite from that era, though it’s not likely a bit I would hold up as one of their best in trying to convey the unique, sometimes groundbreaking comedy that came through the cameras of Late Night with Conan O’Brien. Richter roams the party, asking largely perplexed and wary pop stars if they’ll join his campaign to get Thin Lizzy a tribute segment in the following year’s ceremony. I’m especially delighted every time I watch Richter’s interaction with Melissa Etheridge (“I don’t think it’s funny!”).

So, yeah, I think favorite remains accurate.

Previous entries in this series can be found by clicking on the “Laughing Matters” tag.