I'll have to check out some of his old stuff then. I just assumed he was always that unfunny because I've never seen anything from him but the horrible Tonight Show and that movie with Pat Morita.
Don't know if it will still translate as funny. You need to get in a real eighties mindset. He pioneered the "parents can't work the VCR" bit which has been ripped off a thousand times in a thousand different ways.
I know there are many who are echoing this "he used to be hilarious in the eighties - I *SWEAR*" thing, but it really was true. It was him, Bill Hicks, Teri Garr, Jeff Altman, Brother Theodore, Larry Bud Melman, and a couple of others where if you saw in the listings they were gonna be on Letterman that night, you made sure to tune in. I remember thinking I was damned lucky to go to school in the Midwest in the Central time zone, 'cause it was possible to catch the first one or two guests on Letterman (since he was on an hour earlier) and you could still hit the bars. Whee!
I have no idea if the material translates, in fact, I"m watching some of the old shit on youtube, and it really doesn't. But his whiny "what is
this all about?" regular slob thing is there in it's genesis, and what was once sort of cool and refreshing became the watered down, cafeteria-style denim shirt and jeans version of Jay we see now. He used to wear a lot of pseudo sleazy shawl collar lounge act blazers and shit like that, sort of as though, well, he had to put on a jacket so he's just gonna wear this crazy thing. He really was never very offensive or dangerous, but his observational style really was a cut above the generic guy in front of a brick wall comedy that was pervasive at the time.
Hicks slammed Jay non stop, even back then, if I remember his bits correctly. But then, Hicks was always way too principled, and Jay, well, not nearly enough. Obviously.