Pat Boone: Enter Sandman (Metallica cover)
Richard Cheese: Baby Got Back (Sir Mix-a-Lot cover)
Mike Flowers Pops: Velvet Underground Medley
Pastel Vespa: White Wedding (Billy Idol cover)
Bad cover songs are nothing new. While poking around some of my more horrible examples, I uncovered a multitude of 60s easy listening groups who tried to emulate the groovy sound of what those crazy kids are listening to now! We had the Four Freshmen doing Hurdy Gurdy Man in a pretty funereal style; the Lettermen butchering a Doors medley; the Johnny Mann Singers crooning an utterly soulless take on the Yardbirds' Heart Full of Soul; and an appalling adaptation of Sly and the Family Stone's Everyday People by the Ray Bloch
Zombies Singers. I'm sure there are many, many more "hits" on this wall of shame. Any PBS rerun episode of the Lawrence Welk show will have at least one or two.
Deliberately bad cover songs, though, they're more recent. I'm trying to remember when I first noticed it. Maybe Bill Murray's memorable "Nick the Lounge Singer" character – his first appearance on Saturday Night Live was in 1977; his most famous cover was the Star Wars Theme (with lyrics!).
White-buck-wearing Pat Boone made his career in the 50's covering (some say "ripping off") R&B songs of black artists when radio was segregated. In 1997, he unexpectedly released In a Metal Mood: No More Mr. Nice Guy, an album of metal band covers. Needless to say, it deeply shocked his fans and got him kicked off a gospel show for a time.
Other artists began to embrace satirical stylings, blithely covering alt rock, industrial, hip-hop, metal, or grunge in a deliberately retro style – usually lounge. One well-known singer is Richard Cheese, who probably comes closest to the "Nick" sound. Mike Flowers Pops goes for that immortal Ray Bloch Singers approach, and Pastel Vespa takes it from the female angle.