Warren Zevon
Warren Zevon is most famous for his 1978 album, Excitable Boy, and for hard-rocking, darkly funny tunes like "Werewolves of London," "Lawyers, Guns and Money" and "Roland the Headless Thompson Gunner." Zevon was a songwriter for The Everly Brothers and Linda Ronstadt in the 1960s (he wrote Ronstadt's hit "Poor Poor Pitiful Me") before releasing his first album, Wanted: Dead or Alive in 1969. Zevon was well-regarded by critics and other musicians in the early 1970s but didn't sell many records. Then "Werewolves of London" shot up the charts and by the end of the decade he was a star, known especially for his grim humor and literary lyrics. He also had a reputation as a heavy drinker, but in the early '80s he publicly battled alcoholism and went sober. His subsequent albums never had the success of Excitable Boy, but his fan base remained loyal and he was widely considered a songwriter's songwriter. His other albums included Warren Zevon (1976), Sentimental Hygiene (1987), Mr. Bad Example (1991) and Life'll Kill Ya (2000). In 2002 he announced that he had terminal lung cancer. He managed to record a final album, The Wind, which was released two weeks before his death in September 2003. In 2004 the album earned him his first Grammys, including one for the song "Disorder in the House," a duet with Bruce Springsteen.
Extra credit: In 1990 an album was released featuring Zevon and members of R.E.M. as The Hindu Love Gods... Like Harry Nilsson, Zevon had a song in the Dustin Hoffman movie Midnight Cowboy (1969)... Zevon often filled in as a guest bandleader for David Letterman when regular leader Paul Shafer was absent... After his cancer diagnosis, Zevon famously quipped, "I'm OK with it, but it'll be a drag if I don't make it 'til the next James Bond movie comes out." He did; Die Another Day was released in November 2002.
Somewhat similar semi-cynical songwriters: Lou Reed, Donald Fagen, Frank Zappa.