After all those seasons of The Colbert Report and several months at the helm of The Late Show, Stephen Colbert has proved himself time and again to be one of TV’s most skilled interviewers — which means nothing, however, when an interview goes unexpectedly off the rails, as was the case when actor Casey Affleck dropped by last night to promote his new film Triple 9.

Referencing Affleck’s rumpled clothing, which looked like he selected his outfit by rummaging around in the laundry hamper, Colbert cracked: “Thanks for dressing up. I can’t tell whether this choice is, like, the least celebrity thing to do or the most celebrity thing to do. It’s very casual.”;

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“Thank you,”; replied Affleck, apparently embarrassed by the joke. “You look great.”;

This took Colbert aback: “Well, thank you. I’m not saying you don’t look good. I’m not saying that all,”; as Affleck cut in to call Colbert rude. “I’m not being rude at all,”; said Colbert, describing his jokes as “playful ribbing”; — and then took things one step further by describing Affleck’s look as “a street-corner Jesus.”;

Things only went downhill fro there. Watch what may be Colbert’s most awkward, cringe-inducing interview yet, and don’t forget to tune in to The Late Show with Stephen Colbert, weeknights at 11:35 p.m. on Global.