It’s 3 p.m.! Let The A.V. Club briefly make use of the waning hours of your productivity with some pop culture ephemera pulled from the depths of YouTube.

Owing, at least in part, to its star’s own abiding interest in the art of awkward confrontation, the late, lamented Late Show With David Letterman (and its NBC predecessor, Late Night) played host to some of the least comfortable moments in all of late-night talk. There was the famous Joaquin Phoenix interview, obviously, but also any number of Andy Kaufman stunts, plus decades-worth of other examples of interviews-gone-wrong. Still, we’ve always had a particular soft spot for one Late Show bit where everything appears to have gone exactly as planned, and still created one of the most awkward things ever to be broadcast on CBS’s airwaves.

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We’re talking, specifically, of a 2011 installment of the long-running show, which ended with a major plug for the then-extant Spider-Man musical, Turn Off The Dark. As introduced by Letterman, the bit sees The Green Goblin—Patrick Page, doing his damnedest from beneath a truly unfortunate bit of costuming—“invade” the host’s studio to vamp about how “A Freak Like Me Needs Company.”

For those of you who don’t remember Turn Off The Dark, it was a big-budget Broadway effort that eventually folded after injuring multiple stunt performers, wasting a whole lot of money, and reminding us all that not everything that comes out of Bono’s brain is automatic musical gold. To Page’s credit, “Freak” is merely extremely campy for its first half, even as his Broadway-friendly theatricality clashes maddeningly with the relative intimacy of a talk show set. Things don’t get truly silly until he brings out the “Sinister Six,” some of the goofiest supervillain concepts we’ve ever been privileged to see. The guy in the bee costume is bad, obviously, but pride of place has to go to The Lizard, who appears to be little more than a modified version of one of those T-Rex costumes that always used to pop up in viral videos a few years back.

There’s a lot to enjoy here—Page’s Gene Simmons-esque tongue antics, the bored clapping of the faux-delighted crowd, the embarrassed introduction of scissors-based newcomer “Swiss Miss.” And yet, Letterman still manages to almost save it all with a little dose of his signature snark. Once the number is done, he wanders, like some sort of talk show host tourist, through the crowd of costumed performers, clearly amused at the weirdness of it all. “My god, it’s like a party at my mom’s house,” he notes at one point, passing by implied animal fucker Kraven the Hunter and a sparkler-equipped Electro.

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Still only the second-best bit of Spider-Man-themed content Late Show ever produced, though:

Update: As noted by Some Other Dude Now in the comments, this moment is weird enough to have lodged itself in at least a few influential people’s heads. Thus this (unfortunately grainy) clip from Comedy Bang! Bang!’s second season, featuring an extremely specific parody of this one particular Letterman clip:

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