40s/50s singers attempts to stay hip but mostly failing, sometimes gloriously

e.g. Frank Sinatra’s 'Cycles' album, Ella Fitzgerald covering Cream and Randy Newman.

What else is worth investigating or reassessing?

Posted about this just a couple of days ago:

Peggy Lee is the Bomb

Haven't listened to the album yet, so no opinion. That she covers "Superstar" suggests she was trying to keep up.

Pat Boone does Tim Buckley

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

A guy like Andy Williams did this so routinely that I'm not even sure he counts, but this is filled with covers of Top 40 hits from '72:

https://i.postimg.cc/tCfh4rqX/andy.jpg

He had a live album in '73 with an "Alone Again (Naturally)/Song Sung Blue/The First Time Ever I Saw Your Face/American Pie/Theme from 'Summer of 42'" medley.

XP Album produced by Jerry Yester & finds Boone also covering John Stewart, Biff Rose, Fred Neil, and John D. Loudermilk.

(xpost) Probably tried to talk Columbia into letting him cover "Theme from Shaft," too.

"chequered"

not a 50s band but does "genuine imitation life gazette" count?

Eartha Kitt - Where Is My Man?
https://www.youtube.com/watch?v=n5FJjNSPsgI

also, sammy davis jr must be the all-time king of this, no? his version of "shaft" has him making up his own very swingin' (read corny) lyrics:

"he stands for the good in the roughest neighborhood, he's no stranger (right on!)
he's treated with respect, his friends let him know that there is danger (can you dig it?)"

he also makes up lyrics to the "kojak" theme and provides new lyrics for "love is all around", which are must-hear.

Also, The Ethel Merman Disco Album:
https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEjIokh-Z0J1aQjBACXNWq8wkA_bVi9rv7yRUn9qqefe7XX3Sglzzvo9V7Bkx7_zsjtsocB3FDvC5MUWhxFw3eI2lqZDQB_oYXE-VEvaM-raQ1ecYaAVzwKsP4w_B8dAtm8N8cRlL0DVmUA/s1600/vfvfvffvvfvfvvfv.jpg

Boone apparently had the first commercially released version of "Song To The Siren"!

I like that album cover. I can't decide if the hat in disembodied hand makes it worse or better

oh, also, the velvet fog is not your velvet fool:

https://www.youtube.com/watch?v=YukjHUihvlA

https://www.youtube.com/watch?v=BY0JPKveuok

Jack Jones - “Wives and Lovers” (Disco version)

Probably the most sexist song of all time, but I love it!

also, does louis armstrong doing "the creator has a master plan" count?

https://www.youtube.com/watch?v=LDjDCiTfUnU

That Armstrong album also has a version of "Give Peace a Chance" on it, with Ornette Coleman as one of the backing vocalists.

Not a 40s/50s singer but I still feel compelled to mention Gene Pitney's glorious attempt at swinging late 60s pop, Animal Crackers (in Cellophane Boxes)

Tony Bennett's reluctantly-recorded and instantly disowned 1970 album with modish sleeve art and a few Beatles covers is often put down but I still want to listen to it at some point

https://en.wikipedia.org/wiki/Tony_Sings_the_Great_Hits_of_Today!

"chequered"

― Kate (rushomancy), Wednesday, 3 April 2024 23:39 (yesterday) bookmarkflaglink

Plus this Hendrix/Sly-inspired cut from a few years later

https://www.youtube.com/watch?v=aYQDNVeLXC8

40s/50s singers actors attempts to stay hip but mostly failing, sometimes gloriously
https://www.youtube.com/watch?v=J94-_w9ARX0

which in turn inspired a strange response record - one of the only full-on comedy sketches to chart in the UK

https://www.youtube.com/watch?v=fi5VwDOdSA8

love this album mainly for the cover

https://www.youtube.com/watch?v=qSyHjc6Pif8

https://upload.wikimedia.org/wikipedia/commons/9/90/Howlin%27_Wolf_-_The_Howlin%27_Wolf_Album.jpg

on a smaller timescale, I'm kind of fascinated by the mid to late 60s career of Duane Eddy.
by this point the hits had dried up, so he and producer Lee Hazlewood were grasping at straws to try and reconnect him with "the youth"
so they made an album of Dylan covers in 65, a collection of soft pop hippy hits like Monday Monday and A Groovy Kind Of Love in 66, and a 1920s themed album called The Roaring Twangies in 67. and when that didn't work he made a Japanese only album.

anyway here's Duane & Lee with a crap rewrite of Boots on the hippy album called This Guitar was Made For Twangin'

https://www.youtube.com/watch?v=HIsKxy9MK8A

Wow at the Pat Boone cover! Loving the suggestions.

There’s Link Wray’s very cool and Stones-y ‘70s record

https://www.youtube.com/watch?v=TddkJKg5PNw

Paul Anka, ladies and gents

https://en.wikipedia.org/wiki/Rock_Swings

https://www.youtube.com/watch?v=t0lalWijN_Y

Paul Anka doing It's a Sin wow

Not real, but still.

https://www.youtube.com/watch?v=zUwSaO2SnHQ

There’s Link Wray’s very cool and Stones-y ‘70s record

― President Keyes

wray was genuinely awesome in the '70s, though... like, he wasn't trying, he just _was_ hip

Not a singer, and I think I posted this in another thread recently, but

https://i.discogs.com/6bLZnoynzsnsiqXBUSJf3cVaA9NShNV7-KiX90gYxHc/rs:fit/g:sm/q:90/h:596/w:600/czM6Ly9kaXNjb2dz/LWRhdGFiYXNlLWlt/YWdlcy9SLTIxMDE1/MjEtMTQ4NzYzMDk1/Mi0yMzAyLnBuZw.jpeg

Al Hirt Now!

Jack Jones is still alive! He’s 86. My first radio job at a small town mostly-easy listening station I used to play his cover of Little Feat.

https://www.youtube.com/watch?v=S34OsZs4NHs

Psychedelic Bo Diddley:

https://www.youtube.com/watch?v=4M6uAZl7XjU