Ivana Trump (1949) and John-David Dery (1986)
Status: Possibly Dating
Age Difference: 37 years

Eric Ryan, Getty Images

Ivana Trump (1949) and Rossano Rubicondi (1972)
Status: Divorcing
Age Difference: 23 years

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Robert Wagner (1930) and Barbara Stanwyck (1907)
Status: Dated in the 1950s
Age Difference: 23 years

Hulton Archive / Getty Images

Linda Hogan (1959) and Charlie Hill (1989)
Status: Dating
Age Difference: 29 years

Chris Farina, Wire Image

Bruce Willis (1955) and Emma Heming (1978)
Status: Dating
Age Difference: 23 years

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Ashton Kutcher (1978) and Demi Moore (1962)
Status: Married
Age Difference: 15 years

James Devaney, WireImage.com

Tom Cruise (1962) and Katie Holmes (1978)
Status: Married
Age Difference: 17 years

Kevin Winter, Getty Images

Evan Rachel Wood (1987) and Marilyn Manson(1969)
Status: Dating
Age Difference: 19 years

Scott Wintrow, Getty Images

Reza Jarrahy (1971) and Geena Davis (1956)
Status: Married
Age Difference: 15 years

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Angelina Jolie (1975) and Billy Bob Thornton (1955)
Status: Divorced
Age Difference: 20 years

Vince Bucci, Getty Images

Justin Timberlake told Britney Spears to 'Cry Me A River' after she allegedly cheated on him in 2002.

Jive / Getty Images

After 'Newlyweds' Jessica Simpson and Nick Lachey split in 2005, both have used their music to vent their frustrations. Lachey declared that Simpson could have 'What's Left Of Me,' while she decided to start 'Sipping on History' about "a relationship that could have been."

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Kanye West addresses his heartache about ex-finance Alexis Phifer in the songs 'Love Lockdown' and 'Heartless.'

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'Don't Speak' by No Doubt is about the demise of the relationship between band members Gwen Stefani and Tony Kanal.

Frank Micelotta, ImageDirect / Getty Images

Miley Cyrus tells her ex-beau Nick Jonas the '7 Things' she hates about him. "You're vain, your games, you're insecure. You love me, you like her. You make me laugh, you make me cry."

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Hilary Duff's dark song 'Stranger' is rumored to be about her breakup with Joel Madden.

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Pink sings 'So What' to ex-husband Cary Hart. Her lyrics read, "I guess I just lost my husband. I don't know where he went... so what I'm still a rock star... and I don't need you."

KMazur, WireImage

'You're so Vain' by Carly Simon is mostly about Warren Beatty, but she told FAME Magazine that the song is truly "a composite of three men" from her L.A. days. Other exes who might fit the bill include Mick Jagger, Kris Kristofferson, Cat Stevens and James Taylor.

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Supposedly Paul McCartney wrote the ballad, 'My Soul,' after his divorce from Heather Mills.

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Taylor Swift told Ryan Seacrest that she did a last-minute recording session of the song she wrote about her breakup with Joe Jonas in order to get it on the album.. 'Forever and Always,' is "a song about watching somebody completely fade away in a relationship and wondering what you did wrong," she told People.com.

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TOKYO - OCTOBER 22: Actress Lindsay Lohan poses for photographs at the front row of the Charlotte Ronson Spring/Summer 2009 Fashion Show at the National Stadium on October 22, 2008 in Tokyo. (Photo by Junko Kimura/Getty Images for Charlotte Ronson) *** Local Caption *** Lindsay Lohan

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TOKYO - OCTOBER 22: Actress Lindsay Lohan poses for photographs at the front row of the Charlotte Ronson Spring/Summer 2009 Fashion Show at the National Stadium on October 22, 2008 in Tokyo. (Photo by Junko Kimura/Getty Images for Charlotte Ronson) *** Local Caption *** Lindsay Lohan

Getty Images for Charlotte Ronso

TOKYO - OCTOBER 22: Actress Lindsay Lohan at the front row of the Charlotte Ronson Spring/Summer 2009 Fashion Show at the National Stadium on October 22, 2008 in Tokyo. (Photo by Junko Kimura/Getty Images for Charlotte Ronson) *** Local Caption *** Lindsay Lohan

Getty Images for Charlotte Ronso

TOKYO - OCTOBER 22: Actress Lindsay Lohan at the front row of the Charlotte Ronson Spring/Summer 2009 Fashion Show at the National Stadium on October 22, 2008 in Tokyo. (Photo by Junko Kimura/Getty Images for Charlotte Ronson) *** Local Caption *** Lindsay Lohan

Getty Images for Charlotte Ronso

TOKYO - OCTOBER 22: Actress Lindsay Lohan at the front row of the Charlotte Ronson Spring/Summer 2009 Fashion Show at the National Stadium on October 22, 2008 in Tokyo. (Photo by Junko Kimura/Getty Images for Charlotte Ronson) *** Local Caption *** Lindsay Lohan

Getty Images for Charlotte Ronso

TOKYO - OCTOBER 22: Actress Lindsay Lohan at the front row of the Charlotte Ronson Spring/Summer 2009 Fashion Show at the National Stadium on October 22, 2008 in Tokyo. (Photo by Junko Kimura/Getty Images for Charlotte Ronson) *** Local Caption *** Lindsay Lohan

Getty Images for Charlotte Ronso

TOKYO - OCTOBER 22: Designer Charlotte Ronson (L) and actress Lindsay Lohan walk on the runway of the Charlotte Ronson Spring/Summer 2009 Fashion Show at the National Stadium on October 22, 2008 in Tokyo. (Photo by Junko Kimura/Getty Images for Charlotte Ronson) *** Local Caption *** Charlotte Ronson;Lindsay Lohan

Getty Images for Charlotte Ronso

TOKYO - OCTOBER 22: (L to R) Actress Lindsay Lohan, DJ Samantha Ronson and designer Charlotte Ronson pose for photographs at the backstage of Charlotte Ronson Spring/Summer 2009 Fashion Show at the National Stadium on October 22, 2008 in Tokyo. (Photo by Junko Kimura/Getty Images for Charlotte Ronson) *** Local Caption *** Lindsay Lohan;Samantha Ronson;Charlotte Ronson

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Actress Lindsay Lohan and companion DJ Samantha Ronson seen on the streets of Manhattan on October 14, 2008 in New York City.

Marcel Thomas/FilmMagic.com

Actress Lindsay Lohan and companion DJ Samantha Ronson is seen on the streets of Manhattan on October 14, 2008 in New York City.

Marcel Thomas/FilmMagic.com

Ivana Trump (1949) and Rossano Rubicondi (1972)
Status: Divorcing
Age Difference: 23 years

Getty Images

Robert Wagner (1930) and Barbara Stanwyck (1907)
Status: Dated in the 1950s
Age Difference: 23 years

Hulton Archive / Getty Images

Linda Hogan (1959) and Charlie Hill (1989)
Status: Dating
Age Difference: 29 years

Chris Farina, Wire Image

Bruce Willis (1955) and Emma Heming (1978)
Status: Dating
Age Difference: 23 years

Getty Images

Ashton Kutcher (1978) and Demi Moore (1962)
Status: Married
Age Difference: 15 years

James Devaney, WireImage.com

Tom Cruise (1962) and Katie Holmes (1978)
Status: Married
Age Difference: 17 years

Kevin Winter, Getty Images

Evan Rachel Wood (1987) and Marilyn Manson(1969)
Status: Dating
Age Difference: 19 years

Scott Wintrow, Getty Images

Reza Jarrahy (1971) and Geena Davis (1956)
Status: Married
Age Difference: 15 years

Getty Images

Angelina Jolie (1975) and Billy Bob Thornton (1955)
Status: Divorced
Age Difference: 20 years

Vince Bucci, Getty Images

Paul McCartney (1942) and Heather Mills (1968)
Status: Divorced
Age Difference: 26 years

Todd Williamson, FilmMagic.com