Angelina Jolie and Billy Bob Thornton
Angelina Jolie was married to actor Billy Bob Thornton. They got married in Vegas after 2 months of dating and adopted a child from Cambodia. They soon separated after 2 years of marriage.
Sienna Miller and Jude Law
The couple got engaged on Christmas Day in 2004. But things went south when Jude Law’s infidelity went public. They separated in 2006 but rekindled their relationship in 2009, and it ultimately ended in 2011.
Leonardo Dicaprio and Gisele Bündchen
Before Gisele Bündchen married NFL quarterback Tom Brady, she dated Leonardo Dicaprio from 2000 to 2005.
Zachary Quinto and Jonathan Groff
Quinto came out as gay, publicly, in 2011. The Star Trek actor and Glee star had a relationship from 2010 to 2013.
Cameron Diaz and Justin Timberlake
The actress and singer were together from 2003 to 2007. Cameron Diaz married Good Charlotte band member Benji Madden in 2015. Justin Timberlake married Jessica Biel in 2012.
Natalie Portman and Jake Gyllenhaal
They 2 co-starred in the 2009 film, Brothers, and dated briefly in 2006. The actors remain friends.
January Jones and Ashton Kutcher
Way before Ashton Kutcher and Mila Kunis got married, he dated January Jones in the late ’90s. They were both models for Abercrombie & Fitch.
Brad Pitt and Christina Applegate
These 2 actors had a very brief relationship in 1989. They went on a date to the MTV VMAs, but Christina Applegate actually ditched the Hollywood heartthrob for another man.
Michael Sheen and Rachel McAdams
The Notebook actress and the Underworld actor began dating in 2010 but split up in 2013.
Edward Norton and Salma Hayek
The actors began dating in 1999 after reportedly being set up by their chiropractor. They ended their relationship in 2003.
Cameron Diaz and Alex Rodriguez
These 2 dated for about a year around 2011 but kept their relationship as low-key as possible.
Alanis Morissette and Ryan Reynolds
The Deadpool star and the popular musician were inseparable from the moment they met in 2002. They got engaged in 2004 but never made it down the aisle and broke up in 2007. Ryan Reynolds eventually married Blake Lively in 2012.
Rosario Dawson and Jay Z
It doesn’t ever feel like there was a time when it wasn’t Bey and Jay. But the “99 Problems” rapper and the Seven Pounds actress were linked together back in 2000.
Anne Hathaway and Topher Grace
These 2 starred in the movie Valentine’s Day together but dated way before the movie was made. They were both new to Hollywood and dated from 1999-2001.
Tom Cruise and Penélope Cruz
The Mission: Impossible star dated the Vicky Cristina Barcelona actress from 2001 to 2004.
Bonus: Selena Gomez and Justin Bieber, The Weeknd and Selena Gomez, and The Weeknd and Bella Hadid
Justin Bieber and Selena Gomez had a very public relationship. They had an on-again-off-again relationship over the span of 8 years.
The Weeknd and Selena Gomez were first linked back in 2017. Things ended between them later on that year, but Gomez has said they remain friends.
The Weeknd and Bella Hadid began dating in 2015 after the model appeared in his music video. In 2016, they ended their relationship but dated again in 2018. They eventually called it quits in 2019.