Sorry to ruin your idea Halfshell but A-Log Did it already

madmusic.com/playlist.aspx?Show=AOTA-210724

madmusic.com/playlist.aspx?Show=AOTA-221112

madmusic.com/playlist.aspx?Show=AOTA-210515

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Halfshell:

"Imitations"

Part one: Song Imitations. There's a few comedy/actors stars who tried covers of known songs.
Pee-wee Herman - Surfing Bird

Hulk Hogan - I'm Leader of The Gang

Roseanne Barr - Three Blackbirds

Dennis Haskins -   Friends In Low Places

Jim Carrey - Somebody to Love

i'm sure there's others

Part two: Singers/Actors imitating other actors in their style.

great Luke Ski - Yes We Have No Banana's (Gilbert Gotfried)

Doug Church - Big Dummy (Red Foxx/Fred Sanford)

i'm sure there other examples to this as well

"Imitations"

Part one: Song Imitations. There's a few comedy/actors stars who tried covers of known songs.
Pee-wee Herman - Surfing Bird

Hulk Hogan - I'm Leader of The Gang

Roseanne Barr - Three Blackbirds

Dennis Haskins -   Friends In Low Places

Jim Carrey - Somebody to Love

i'm sure there's others

Part two: Singers/Actors imitating other actors in their style.

great Luke Ski - Yes We Have No Banana's (Gilbert Gotfried)

Doug Church - Big Dummy (Red Foxx/Fred Sanford)

i'm sure there other examples to this as well