Take The Money And Run: The 20 Costliest Divorces In Music History

We ain't saying she a gold digger...

I think we can all agree that love is pretty great. That is, until that love turns to hate, hate to legal documents, and legal documents into mega cash settlements. Welcome to divorce, American style!

Some long-time music marriages resulted in major payouts, but then there were some who made bank in the blink of an eye. There was Paul McCartney’s infamous union to Heather Mills, but the title for the quickest goes to back-up dancer Cris Judd, was only married to Jennifer Lopez for just 8 months! And we can’t forget Janet Jackson’s marrage to Rene Elizondo, Jr., which was kept so secret that we didn’t even know about it until after the divorce was finalized.

It’s true that sometimes love does go bad, and these artists prove that tickets to Splitsville don’t come cheap. Head to the gallery below for the 20 of the biggest divorce settlements ever. In the words of Kanye West, “We want prenup!”

  • 1 Russell Simmons and Kimora Lee-Simmons
    Russell Simmons and Kimora Lee-Simmons (1998-2009): After 11 years of marriage and two kids Russell and Kimora ended their relationship. Russell was ordered to pay $40,000 per month in child support until their daughters turn 19.

  • 2 Nas and Kelis
    Nas and Kelis (2005-2010) The former king and queen of hip hop ended their marriage because of irreconcilable differences. After the divorce was settled Nas was ordered to pay $51,000 per month in back child support, $10,000 per month in spousal support, and he had to pay Kelis’ legal fees of $200,000.

  • 3 Britney Spears and Kevin Federline
    Britney Spears and Kevin Federline (2004-2007) After a tumultuous divorce and custody battle Britney lost custody of their two boys. She was also order to pay Kevin $1 million and $40,000 per month in child support.

  • 4 Jessica Simpson and Nick Lachey
    Jessica Simpson and Nick Lachey (2002-2006) Simpson’s father apparently offered Lachey $1.5 million but he turned it down.

  • 5 The Dream and Christina Milian
    The Dream and Christina Milian (2009-2011) After 10 months of marriage The Dream and Milian filed for divorce. Dream was ordered to paid $4 million and $5,000 per month in child support for their daughter.

  • 6 Dan Auerbach and Stephanie Gonis
    Dan Auerbach and Stephanie Gonis(2013) After a very trying divorce Auerbach had to pay Gonis $5 million and give up the lock of Bob Dylan’s hair that they owned.

  • 7 Ronnie Wood and Jo Wood
    Ronnie Wood and Jo Wood (1985-2009) Ronnie paid an estimated $9.9 million to Jo when their divorce was finalized.

  • 8 Janet Jackson and Rene Elizondo
    Janet Jackson and Rene Elizondo (1991-2000) After being secretly married for 13 years, Janet and Rene divorced. It is reported that Janet had to pay Rene $10 million in the settlement.

  • 9 Mick Jagger and Jerry Hall
    Mick Jagger and Jerry Hall (1990-1999) Mick Jagger paid Jerry Hall $10 million after their common-law marriage ended.

  • 10 Rod Stewart and Rachel Hunter
    Rod Stewart and Rachel Hunter (1990-2006) It is rumored that Rod paid $12.3 million in the divorce settlement.

  • 11 Jennifer Lopez and Chris Judd
    Jennifer Lopez and Chris Judd (2001-2002) After 8 months of marriage, Judd, a backup dancer and choreographer, hit the jackpot. Lopez reportedly had to pay Judd $14 million in their divorce settlement.

  • 12 Bruce Springsteen and Julianne Phillips
    Bruce Springsteen and Julianne Phillips (1985 – 1989) Springsteen paid $20 million in the divorce settlement.

  • 13 Lionel Richie and Diana Richie
    Lionel Richie and Diana Richie (1995 – 2004) Lionel paid Diana $20 million which was less then what she had requested.

  • 14 Elton John and Renate Blauel
    Elton John and Renate Blauel (1984 – 1988) John paid his ex-wife, Renate $45 million to end their brief marriage.

  • 15 Phil Collins and Orianne Cevey
    Phil Collins and Orianne Cevey (1999 – 2008) Collins ended his third marriage for $46.76 million. This brought his divorce settlement total up to $84 million. Guess he didn’t learn the first two times.

  • 16 Paul McCartney and Heather Mills
    Paul McCartney and Heather Mills(2002 – 2008) When McCartney and Mills filed for divorce, Mills wanted $250 million of McCartney’s fortune. She ended up getting $48.6 million.

  • 17 Kenny Rogers and Marianne Gordon
    Kenny Rogers and Marianne Gordon(1977-1993) Kenny Rogers is currently on his fifth marriage but the marriage that will go down in history is his fourth to Marianne Gordon. After 16 years together, Gordon received a $60 million divorce settlement.

  • 18 Madonna and Guy Ritchie
    Madonna and Guy Ritchie(2000-2008) When Madonna anf Guy divorced, Madonna had to give Guy $76-92 million in the divorce settlement.The actual amount has not been determined because the home and pub that the couple owned in England were passed to Ritchie in the settlement.

  • 19 Garth Brooks and Sandy Mahl
    Garth Brooks and Sandy Mahl(1986-2001) After 14 years of marriage, the college sweethearts called it quits. It was rumored that Brooks had an affair with Trisha Yearwood but the two denied the alligations. Either way, Mahl was awarded $125 million as a divorce settlement.

  • 20 Neil Diamond and Marcia Murphey
    Neil Diamond and Marcia Murphey(1969-1994) When Diamond and Murphey got divorced, he had to give her half of his fortune, $150 million. While most men would be pretty bummed, Diamond reportedly said, “she’s worth every penny”.

VH1 Music Editor + Seltzer Enthusiast
@jordanruntagh