We used to play this game by "type" so...

Musicians (and a poet)
Waylon Jennings (Goodman & Prine)
Charley Pride (id.)
Merle Haggard (id.)
David Allen Coe (id.)
Brenda Lee (Hay & Kooymans)
Sidney Bechet (Patricia Kaas)
Frankie D (Guy Clark)
Roger Miller (id.)
Ramblin' Jack Elliot (id.)
Larry Mahan (id.)
Anita Bryant (Jimmy Buffett)
Patsy Cline (Jimmy Buffett; Emmylou Harris)
Bo Diddley (Bo Diddley)
Mama Cass (Phillips & Gilliam)
Dwight Yoakam (Mary Chapin Carpenter)
Lyle Lovett (id.)
Johnny Rotten (Neil Young)
Charlie Watts (John Hiatt)
T.S. Eliot (Brad Roberts – Crash Test Dummies)

Actors
Bob Hope (Billy Joel)
Carol Merrill (Jimmy Buffett)
Richard Pryor (Jackson Browne)
Lotte Lenya (Bobby Darin)
Betty Davis (Donna Weiss & Jackie De Shannon)
Jean Harlow (id.)
Greta Garbo (id.)
Tuesday Weld (Donald Fagen)
Bette Davis (Mark Knopfler)
Charlie & Oona Chaplin (Steve Forbert)
Warren Beatty (id.)

Sports
Joe DiMaggio (John Fogerty; Paul Simon)
Dale Earnhardt (John Hiatt)
Red Grange (Weston & Weston)

Politics (etc)
Rose Kennedy (Patricia Kaas)
George Murphy (Tom Lehrer)
Wernher von Braun (id.)
Eva Braun (Danny O'Keefe)
Harry Truman (id.)
Henry VIII (Murray & Weston)
Anne Boleyn (John Popper; Weston & Weston)

Characters
Oedipus Rex (Tom Lehrer)
Rita Ballou (Guy Clark)
Spider John (Willis Alan Ramsey)
Mona Lisa (Emmylou Harris; Livingston & Evans)
Charlie Brown (Clark M. Gesner; Leiber & Stoller)
Polk Salad Annie (Tony Joe White)

More to follow...