Hosted: once (1994)
The expectation was that Letterman, having the crown of late night television handed to him by Johnny Carson, would excel at the Oscar hosting gig, just as Carson had. This didn’t happen, for two reasons. Letterman has the arrogance of ego, but no comfort level with it. He’s essentially a nervous, awkward man, lacking the flexibility that’s required to go outside his own comfort zone. He’s warm with pretty girls, but put him next to a touchy-feely kind of fellow like, say, Colin Farrell, and watch him squirm. Second, he’s also, in his way, utterly ignorant of Hollywood, and proud of it. Part of his shtick on the “Late Show” is to play the ignorant buffoon (“Now Jennifer, are you married to that Pitt fellow?”). But the undercurrent is and always has been: This is nonsense, why should I care? Nor did his love of the sophomoric gimmick translate. (Remember that “Cabin Boy” “audition” clip? Even Paul Newman couldn’t transcend its stupidity.) But, in his defense, the bit that is oft-cited as the reason for him being the Worst Host Ever, that “Uma, meet Oprah, Oprah meet Uma” thing, was not as daffy and pointless as it seemed back at the time. Thanks to Nikke Finke, those of us who are less well-educated in comedy history than Letterman now know he was referencing a famous “Yma” bit by Anne Bancroft, from her 1970 television special. Should have saved that for an Emmy’s telecast, Dave. On the upside, Letterman has made it clear he’s never coming back.
Overall impression: Clod in a good suit.