D-Day: The Ugliest Celebrity Divorces

Stars who have been through nasty splits.

The End of the Road - It's a sad fact that most celebrity marriages wind up in divorce, so picking the worst of the worst was no easy task.Roc-a-Fella Records co-founder Damon Dash married then up-and-coming designer Rachel Roy in 2005 while she worked at Rocawear. Four years later, Roy filed for divorce. Following the split, much hasn't been heard about the former couple, until recently. Roy received full custody of their two daughters in April 2015 and days later, Dash fired back, filing a lawsuit, accusing her of interfering with his earnings.(Photo: Evan Agostini/Getty Images For Tribeca Film Festival) 

1 / 21

The End of the Road - It's a sad fact that most celebrity marriages wind up in divorce, so picking the worst of the worst was no easy task.Roc-a-Fella Records co-founder Damon Dash married then up-and-coming designer Rachel Roy in 2005 while she worked at Rocawear. Four years later, Roy filed for divorce. Following the split, much hasn't been heard about the former couple, until recently. Roy received full custody of their two daughters in April 2015 and days later, Dash fired back, filing a lawsuit, accusing her of interfering with his earnings.(Photo: Evan Agostini/Getty Images For Tribeca Film Festival) 

Dwyane Wade vs. Siohvaughn Funches - NBA all-star Dwyane Wade's legal battle with his ex-wife, Siohvaughn Funches, seemed to last for an eternity, but the former couple reached a settlement in 2013 that put it all to rest. Wade agreed to pay Funches $5 million, in addition to giving up their Chicago mansion, four cars, and a "non-disparage" agreement where both parties are legally prohibited from publicly shaming each other. The NBA star is now happily married to Being Mary Jane star Gabrielle Union.(Photo: Frazer Harrison/Getty Images)

2 / 21

Dwyane Wade vs. Siohvaughn Funches - NBA all-star Dwyane Wade's legal battle with his ex-wife, Siohvaughn Funches, seemed to last for an eternity, but the former couple reached a settlement in 2013 that put it all to rest. Wade agreed to pay Funches $5 million, in addition to giving up their Chicago mansion, four cars, and a "non-disparage" agreement where both parties are legally prohibited from publicly shaming each other. The NBA star is now happily married to Being Mary Jane star Gabrielle Union.(Photo: Frazer Harrison/Getty Images)

Swizz Beatz vs. Mashonda - After four years of marriage, super producer Swizz Beatz and Mashonda ended their marriage in April 2008. Just a year later, it was confirmed that Beatz was romantically tied to R&B singer Alicia Keys, and in 2010, the pair got engaged and revealed that they were pregnant with their first child together. The swiftness of their engagement and Keys's pregnancy prompted many to believe that the pair was dating while he was still married to Mashonda.(Photo: Paul Hawthorne/Getty Images)

3 / 21

Swizz Beatz vs. Mashonda - After four years of marriage, super producer Swizz Beatz and Mashonda ended their marriage in April 2008. Just a year later, it was confirmed that Beatz was romantically tied to R&B singer Alicia Keys, and in 2010, the pair got engaged and revealed that they were pregnant with their first child together. The swiftness of their engagement and Keys's pregnancy prompted many to believe that the pair was dating while he was still married to Mashonda.(Photo: Paul Hawthorne/Getty Images)

Kevin Hart vs. Torrei Hart - Kevin Hart's divorce from his now ex-wife, Torrei Hart, was finalized in November 2011. Though he received joint custody of their two children, things weren't all great with the former lovers. Torrei joined the cast of the VH1 reality series Atlanta Exes in 2014, revealing that she was there for the now A-list comedian when he was "still a nobody." She even accused his new fiancée, Eniko Parrish, of contributing to their split. All is well now, however, as the reality star was seen showing off her new Escalade gifted to her by her movie star ex. (Photo: Francis Specker /Landov)

4 / 21

Kevin Hart vs. Torrei Hart - Kevin Hart's divorce from his now ex-wife, Torrei Hart, was finalized in November 2011. Though he received joint custody of their two children, things weren't all great with the former lovers. Torrei joined the cast of the VH1 reality series Atlanta Exes in 2014, revealing that she was there for the now A-list comedian when he was "still a nobody." She even accused his new fiancée, Eniko Parrish, of contributing to their split. All is well now, however, as the reality star was seen showing off her new Escalade gifted to her by her movie star ex. (Photo: Francis Specker /Landov)

Robin Thicke vs. Paula Patton - After 21 years together and almost nine years of marriage, Paula Patton officially divorced Robin Thicke in March 2015. The big decision was prompted by months of speculation that the R&B star was cheating, abusing drugs, and blinded by fame. Thicke attempted to win the actress back by naming his seventh studio album after her, but both the album and his corny attempt at reconciliation tanked — hard.(Photo: Larry Busacca/Getty Images for NARAS)

5 / 21

Robin Thicke vs. Paula Patton - After 21 years together and almost nine years of marriage, Paula Patton officially divorced Robin Thicke in March 2015. The big decision was prompted by months of speculation that the R&B star was cheating, abusing drugs, and blinded by fame. Thicke attempted to win the actress back by naming his seventh studio album after her, but both the album and his corny attempt at reconciliation tanked — hard.(Photo: Larry Busacca/Getty Images for NARAS)

ADVERTISEMENT
Sherri Shepherd vs. Lamar Sally - Following their marriage in 2011, Sherri Shepherd found herself edging along the trail of divorce after her estranged husband, Lamar Sally, filed in 2014. Though their divorce is yet to be finalized, the couple drama continued with a surrogate that they hired giving birth to their child before the filing. The former co-host of The View claimed that Sally tricked her into the surrogacy process, and refused to claim the child. However, that was all put to rest in April 2015 when a judge ruled that Shepherd was the mother of the baby boy. She is now required to pay child support to her soon-to-be ex-husband.(Photo: Donna Ward/Getty Images)

6 / 21

Sherri Shepherd vs. Lamar Sally - Following their marriage in 2011, Sherri Shepherd found herself edging along the trail of divorce after her estranged husband, Lamar Sally, filed in 2014. Though their divorce is yet to be finalized, the couple drama continued with a surrogate that they hired giving birth to their child before the filing. The former co-host of The View claimed that Sally tricked her into the surrogacy process, and refused to claim the child. However, that was all put to rest in April 2015 when a judge ruled that Shepherd was the mother of the baby boy. She is now required to pay child support to her soon-to-be ex-husband.(Photo: Donna Ward/Getty Images)

Deion Sanders vs. Pilar Sanders - NFL star Deion Sanders's split from wife Pilar is one for the books. It started with the standard decision to "remain friends," but that quickly dissolved into mutual allegations of abuse, police involvement and jail time. The best part? These two bitter exes are still living under the same roof.(Photo: UPI Photo /Landov)

7 / 21

Deion Sanders vs. Pilar Sanders - NFL star Deion Sanders's split from wife Pilar is one for the books. It started with the standard decision to "remain friends," but that quickly dissolved into mutual allegations of abuse, police involvement and jail time. The best part? These two bitter exes are still living under the same roof.(Photo: UPI Photo /Landov)

Allen Iverson vs. Tawanna Iverson - They were high school sweethearts, but in 2011 Tawanna decided she had enough of being a basketball wife and filed for divorce. The Answer tried to pull the plug on their split in 2014, claiming he and Tawanna were still living like man and wife, but his ex retaliated by asking a judge for a restraining order against Iverson's "threatening" behavior.(Photo: REUTERS/Gary Hershorn /Landov)

8 / 21

Allen Iverson vs. Tawanna Iverson - They were high school sweethearts, but in 2011 Tawanna decided she had enough of being a basketball wife and filed for divorce. The Answer tried to pull the plug on their split in 2014, claiming he and Tawanna were still living like man and wife, but his ex retaliated by asking a judge for a restraining order against Iverson's "threatening" behavior.(Photo: REUTERS/Gary Hershorn /Landov)

Kim Kardashian vs. Kris Humphries - The wedding seen 'round the world turned into a divorce, just 72 days later. Kim's split from NBA player Humphries got more and more twisted with each day as Humphries tried his hardest to prove his ex-wife is a fraud who only married him for ratings. After the divorce was finalized, both parties moved on with their lives, with Kim marrying rapper Kanye West a year later, in 2014.(Photo: Fame Pictures)

9 / 21

Kim Kardashian vs. Kris Humphries - The wedding seen 'round the world turned into a divorce, just 72 days later. Kim's split from NBA player Humphries got more and more twisted with each day as Humphries tried his hardest to prove his ex-wife is a fraud who only married him for ratings. After the divorce was finalized, both parties moved on with their lives, with Kim marrying rapper Kanye West a year later, in 2014.(Photo: Fame Pictures)

Tiger Woods vs. Elin Nordegren - The mighty fell hard in 2009 when Woods was exposed for his numerous (understatement!) extramarital affairs. His Swedish model wife filed for divorce in early 2010, taking half the sports legend's fortune and forever shattering the illusion of their picture-perfect marriage. (Photo: Harry How/Getty Images)

10 / 21

Tiger Woods vs. Elin Nordegren - The mighty fell hard in 2009 when Woods was exposed for his numerous (understatement!) extramarital affairs. His Swedish model wife filed for divorce in early 2010, taking half the sports legend's fortune and forever shattering the illusion of their picture-perfect marriage. (Photo: Harry How/Getty Images)

ADVERTISEMENT
Star Jones vs. Al Reynolds - The "corporate sponsorships" of their wedding not only cost Star her job on The View, it was a bad sign for her marriage to investment banker Reynolds. Star served Al his walking papers in early 2008, with insiders revealing she resented him for riding on her success. Double-edged sword, ain't it, Star? (Photo: Bryan Bedder/CP/Getty Images)

11 / 21

Star Jones vs. Al Reynolds - The "corporate sponsorships" of their wedding not only cost Star her job on The View, it was a bad sign for her marriage to investment banker Reynolds. Star served Al his walking papers in early 2008, with insiders revealing she resented him for riding on her success. Double-edged sword, ain't it, Star? (Photo: Bryan Bedder/CP/Getty Images)

Terrence Howard vs. Michelle Ghent - Howard's latest divorce (his third) is turning out to be his messiest, with the exes accusing each other of physical abuse, racial slurs, threats and Ghent telling lawyers Howard had a secret "second cellphone" throughout their marriage. Salt in the wound? Howard was ordered to give his ex $50,000 to hold her over until a divorce settlement is reached. Which, at this pace, will take longer than their one-year union.(Photo: Michael Buckner/Getty Images)

12 / 21

Terrence Howard vs. Michelle Ghent - Howard's latest divorce (his third) is turning out to be his messiest, with the exes accusing each other of physical abuse, racial slurs, threats and Ghent telling lawyers Howard had a secret "second cellphone" throughout their marriage. Salt in the wound? Howard was ordered to give his ex $50,000 to hold her over until a divorce settlement is reached. Which, at this pace, will take longer than their one-year union.(Photo: Michael Buckner/Getty Images)

The-Dream vs. Christina Milian - Things between these two music stars looked as though it hit rock-bottom when Dream filed for divorce just nine days before Milian gave birth to their first child. It got considerably uglier, however, when he realized he would have to give his ex 10 percent of the cash he made from co-writing Justin Bieber's hit "Baby." Milian has been outspoken about her failed marriage — especially on her new E! reality show — which she called "hell," but both parties finally seem to have moved on.(Photo: Michael Loccisano/Getty Images)

13 / 21

The-Dream vs. Christina Milian - Things between these two music stars looked as though it hit rock-bottom when Dream filed for divorce just nine days before Milian gave birth to their first child. It got considerably uglier, however, when he realized he would have to give his ex 10 percent of the cash he made from co-writing Justin Bieber's hit "Baby." Milian has been outspoken about her failed marriage — especially on her new E! reality show — which she called "hell," but both parties finally seem to have moved on.(Photo: Michael Loccisano/Getty Images)

Kobe Bryant vs. Vanessa Bryant - They weathered the storm of Kobe's 2003 "sexual encounter" with a Denver hotel employee (thanks in part to a massive diamond), but things fell apart in 2014 after Vanessa allegedly discovered the cheating never stopped. However, the exes are looking more than friendly recently, and were even caught kissing near the Lakers' locker room on Valentine's Day. (Photo: REUTERS/Danny Moloshok/Landov)

14 / 21

Kobe Bryant vs. Vanessa Bryant - They weathered the storm of Kobe's 2003 "sexual encounter" with a Denver hotel employee (thanks in part to a massive diamond), but things fell apart in 2014 after Vanessa allegedly discovered the cheating never stopped. However, the exes are looking more than friendly recently, and were even caught kissing near the Lakers' locker room on Valentine's Day. (Photo: REUTERS/Danny Moloshok/Landov)

Michael Jordan vs. Juanita Jordan - After years of alleged infidelity, the NBA legend had the most expensive divorce in history in 2007 when he had to pay his ex, Juanita, $20 million to dissolve their 17-year marriage. But the baller still believes in love... He got engaged to girlfriend Yvette in 2013. (Photo: Tim Boyle/Newsmakers)

15 / 21

Michael Jordan vs. Juanita Jordan - After years of alleged infidelity, the NBA legend had the most expensive divorce in history in 2007 when he had to pay his ex, Juanita, $20 million to dissolve their 17-year marriage. But the baller still believes in love... He got engaged to girlfriend Yvette in 2013. (Photo: Tim Boyle/Newsmakers)

ADVERTISEMENT
Jennifer Lopez vs. Marc Anthony - We still don't know the true reason behind J.Lo's shocking split from Marc Anthony in 2014 (force of habit?), but their post-split behavior seems to swing from business-cordial to outright nasty with every passing day. Jennifer rebounded with 24-year-old dancer Casper Smart, but the pop star is now single and ready to mingle yet again.(Photo: Albert L. Ortega/PictureGroup)

16 / 21

Jennifer Lopez vs. Marc Anthony - We still don't know the true reason behind J.Lo's shocking split from Marc Anthony in 2014 (force of habit?), but their post-split behavior seems to swing from business-cordial to outright nasty with every passing day. Jennifer rebounded with 24-year-old dancer Casper Smart, but the pop star is now single and ready to mingle yet again.(Photo: Albert L. Ortega/PictureGroup)

Eva Longoria vs. Tony Parker - The real-life drama of Eva's divorce from NBA player Parker rivaled that of Desperate Housewives. Longoria filed papers after discovering hundreds of sexts between her hubby and his teammate's wife. Longoria, who was "heartbroken" after the split, rebounded quickly in the arms of Penélope Cruz's younger bro, Eduardo.(Photo: Gregg DeGuire/PictureGroup)

17 / 21

Eva Longoria vs. Tony Parker - The real-life drama of Eva's divorce from NBA player Parker rivaled that of Desperate Housewives. Longoria filed papers after discovering hundreds of sexts between her hubby and his teammate's wife. Longoria, who was "heartbroken" after the split, rebounded quickly in the arms of Penélope Cruz's younger bro, Eduardo.(Photo: Gregg DeGuire/PictureGroup)

Being Bobby Brown - Whitney stole the spotlight once again when she appeared on husband Bobby Brown's Bravo reality show, Being Bobby Brown. But, while she hoped it would show fans that her life and marriage were intact, the effect was quite the opposite. (Photo: L. Cohen/WireImage)

18 / 21

Whitney Houston vs. Bobby Brown - When Houston decided to clean up her life and refocus on her music, part of the process was ending her turbulent 15-year marriage to Bobby Brown. The late singer told Oprah in 2009 that the final decision to divorce came from her then-13-year-old daughter, Bobbi Kristina, who told her, after years of disappointment, to "let him go."(Photo: L. Cohen/WireImage)

Lionel Richie vs. Brenda Harvey - Richie's first ex-wife let her anger get the best of her when she caught the singer and his lady-friend Diane (who would later become the second ex-Mrs. Richie) in a tryst at the Beverly Hills Hotel. She reportedly attacked the canoodling couple and was subsequently arrested for spousal abuse.(Photo: Ron Galella, Ltd./WireImage)

19 / 21

Lionel Richie vs. Brenda Harvey - Richie's first ex-wife let her anger get the best of her when she caught the singer and his lady-friend Diane (who would later become the second ex-Mrs. Richie) in a tryst at the Beverly Hills Hotel. She reportedly attacked the canoodling couple and was subsequently arrested for spousal abuse.(Photo: Ron Galella, Ltd./WireImage)

Photo By Photo: Ron Galella

Halle Berry vs. Eric Benét - It's no secret that Berry has been unlucky in love, but her most heartbreaking split was with Benét, who she once thought was a "sensitive" man and "unlike any other man" she'd been with. Unfortunately, the couple divorced in 2003 after years of his infidelity. Nearly a decade later, Berry is giving marriage another chance with her new husband, Olivier Martinez. (Photo: Vince Bucci/Getty Images)

20 / 21

Halle Berry vs. Eric Benét - It's no secret that Berry has been unlucky in love, but her most heartbreaking split was with Benét, who she once thought was a "sensitive" man and "unlike any other man" she'd been with. Unfortunately, the couple divorced in 2003 after years of his infidelity. Nearly a decade later, Berry is giving marriage another chance with her new husband, Olivier Martinez. (Photo: Vince Bucci/Getty Images)

Janet Jackson vs. Renee Elizondo - Jackson managed to keep her nine-year marriage to Elizondo a secret, but their contentious divorce became very public when Elizondo disputed their pre-nup and sued Jackson for spousal support. Though neither party confirmed what the final settlement was, reports range anywhere from $10 million to $100 million. The pop icon gave marriage another try in 2013, marrying Qatari billionaire Wissam Al Mana.(Photo: Jim Smeal/WireImage)

21 / 21

Janet Jackson vs. Renee Elizondo - Jackson managed to keep her nine-year marriage to Elizondo a secret, but their contentious divorce became very public when Elizondo disputed their pre-nup and sued Jackson for spousal support. Though neither party confirmed what the final settlement was, reports range anywhere from $10 million to $100 million. The pop icon gave marriage another try in 2013, marrying Qatari billionaire Wissam Al Mana.(Photo: Jim Smeal/WireImage)