Gary Dell'Abate A.K.A. "Baba Booey" from The Howard Stern Show. He got that nickname over twenty years ago for pronouncing a cartoon character's name wrong, and that's probably one of the nicer things that's happened to him over the years.
Karl Pilkington in Ricky Gervais' radio and podcast series, The Ricky Gervais Show. Despite it being Gervais' goal to make Pilkington a bona fide star, he introduces him as "a shaven monkey with a head like a f*** ing orange", and it all goes downhill from there.
Bluebottle from The Goon Show (though there's a reasonable number of Goon Shows where the whole cast dies, or is screwed over).
Neddy Seagoon probably qualifies too, given that he's usually the target of Grytpype-Thynne's schemes.
Greg T, the Round Headed Frat Boy, of Elvis Duran and the Z100 Morning Zoo in New York.