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The sensational singer Madonna has been divorced twice and in failed relationships a couple of times.
Over the years, Johnny Depp has been in numerous failed relationships with stars like Kate Moss and his infamous divorce with Amber Heard.
Singer Katy Perry has been divorced once to Russell Brand and has been through several breakups including her recent split from Orlando Bloom.
Singer and actress Jennifer Lopez has been thrice divorced and even called off her engagement to actor Ben Affleck back in the early 2000's.
Sensational popstar Taylor Swift is known for her highly public and some messy breakups with stars like Harry Styles, Joe Alwyn, and Joe Jonas, to name a few.
The 2000's diva popstar Britney Spears has been divorced twice following very short-lived marriages, along with several failed public relationships.
Diva actress Angelina Jolie has seen three failed marriages including her divorce with Brad Pitt, along with several other unsuccessful relationships.
Renowned Hollywood personality Paris Hilton has been in many public breakups including a broken engagement with Zylka.
The heartthrob actor Brad Pitt has been divorced twice, to Angelina Jolie and Jennifer Aniston. He has also been in many public relationships which turned out to be a disaster.
Talented actress Lindsay Lohan has been in several messy breakups and even a broken engagement to Egor Tarabasov throughout her career in Hollywood.