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Most embarrassing attempt at being "hip"

If we are going to veer off into lame cover versions, we MUST mention William Shatner, which, unless I missed it, no one has mentioned him. I will, however, give him a pass, because it does not appear to me that he was trying to be "hip" or "with it," and that his albums of cover versions were just caricatures or "send-ups," and never really meant to be taken seriously. If anyone has any evidence to the contrary, please feel free to post it.
 
Tony Bennett had a brief appearance in Adam Sandler's "Anger Management" as himself. If that's not a nod to the MTV generation, I don't know what is. (BTW, my dad tells a story of being in Detroit on a night when Bennett was performing there; the lines outside the theater were made up mainly of people who looked to be under 30.)

And believe it or not, Pat Boone made the Billboard charts with his covers of Fats Domino and Little Richard records; at the time, the fact that Boone was white made him a little more palatable with adults, something very few people would even think about today. And oldies radio stations play the originals, not his covers.
(I'm still working on how Lawrence Welk let him sing the downbeat "Moody River" on a 1961 Welk show; although not a cover, it does tell the story of a woman who drowned herself over her infidelity to Boone or the person he plays in the song, although I'm not sure if they were supposed to be married or boyfriend-girlfriend. Nevertheless, it was more downbeat than anything Welk usually featured.)
 
Welk apparently did not listen to the lyrics. He also played "One Toke Over The Line" on his show. Maybe he thought it was a spiritual.

Surprising that Welk had guest stars, especially one that well known.

And during the 60s and after, Welk did increasingly feature country music (and country artists) on his show.

Much of early rock was covers by White artists of R&B material (including Bill Haley and Elvis). When rock started to take off, many country artists were hired to cover R&B songs because, it was felt, they were the only ones who could give the material the same kind of edge the original Black artists did.
 
This proves that rock and roll was dominant on Welk's show even surf music.

Here are The Chantays performing their song "Pipeline" on Lawrence Welk's show in May 1963.

https://www.youtube.com/watch?v=-NwQv9EZ7Uw

Then there's The Beach Boys' appearance from 1965 on Jack Benny's show featuring Jack and Bob Hope dressed up as surfers. This Jack Benny show is in the public domain in its black and white kinescope so it's very easy to find.

Here it is in color and in much better quality. It starts at 9:00

https://www.youtube.com/watch?v=77iQUBecTyU
 
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If we are going to veer off into lame cover versions, we MUST mention William Shatner, which, unless I missed it, no one has mentioned him. I will, however, give him a pass, because it does not appear to me that he was trying to be "hip" or "with it," and that his albums of cover versions were just caricatures or "send-ups," and never really meant to be taken seriously. If anyone has any evidence to the contrary, please feel free to post it.

Bill Cosby had several albums where he sang, but it was made to be for laughs.
 
Now that you mention Shatner, I was flipping through channels on the weekend a few years ago and he was performing a "lounge singer version" of Cee-Lo Green's "Forget You" (the unedited version)...I know the show he was on aired one of the cable news channels, and that show got cancelled pretty quickly, but what show was he appearing on?
 
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