I’ve always loved “clueless” television characters for the sublimely uncomfortable moments they create. One of my all-time favorites in this regard is Hank Kingsley, played by Jeffrey Tambor on HBO’s The Larry Sanders Show in the ’90s.

In the HBO series, Hank is the bumbling second banana on a nighttime talk show starring Larry Sanders (Garry Shandling).

I stumbled across this clip on YouTube. In it Hank is meeting the members of East Coast hip hop collective Wu Tang Clan before their appearance that night on the Sanders show. (You’ll also see Jon Stewart in the clip. Stewart, playing himself, often filled in as guest-host on Larry’s show.)

It’s been years since I’ve seen this, but the part I remembered was Hank commiserating with the Clan about Da Man after being told that Ol’ Dirty Bastard just got out of jail (“I know that dig, y’know? I got parking tickets coming right out of my ass. Fuckers. Cops, y’know? Fuckers!”).

After Hank leaves, Stewart is compelled to apologize “on behalf of all my people.”

This clip comes from Season 6, Episode 6. It’s on the Not Just the Best of the Larry Sanders Show DVD collection, which you can rent on Netflix.