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Not every celebrity couple is as memorable as Brad Pitt and Jennifer Aniston or Reese Witherspoon and Ryan Phillippe (R.I.P.). And unless a pair was lucky enough to be bestowed with a supercouple moniker like Bennifer, Brangelina, TomKat and (who could possibly forget?) Speidi, we tend to block from our memories some of the oddest celeb romances that ever existed. From Nicole Kidman and Lenny Kravitz to Jessica Biel and Chris Evans, here are 11 shocking A-list couples who once upon a time ruled the red carpet.

Jessica Biel Chris Evans
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1. Jessica Biel & Chris Evans

Before she was Mrs. Justin Timberlake, Jessica Biel dated what’s-his-face (at the time) Chris Evans. The couple made several public appearances over the course of their five-year relationship and even starred alongside each other in the films Cellular and London. Although they never revealed the reason behind their split, Evans and Biel officially called it quits in June 2006.

Ryan Gosling Sandra Bullock
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2. Sandra Bullock & Ryan Gosling

In 2002, Sandra Bullock met 22-year-old Ryan Gosling on the set of Murder by Numbers. Despite their—wait for it—16-year age difference, the pair dated briefly and mutually ended their relationship in 2003. A handsome couple indeed.

Ryan Reynolds Alanis Morrisette
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3. Alanis Morissette & Ryan Reynolds

Alanis Morissette and Ryan Reynolds met when they attended Drew Barrymore’s 27th birthday party in 2002. Following their meet-cute, the couple became practically inseparable, and Reynolds popped the question two years later. Luckily for Blake Lively, the pair called off their engagement in 2007 and Morissette went on to write an album, Flavors of Entanglement, about the one that got away. Well, isn’t that ironic?

Sophia Bush Chad Michael Murray
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4. Sophia Bush & Chad Michael Murray

Much like their One Tree Hill characters, Sophia Bush and Chad Michael Murray weren’t meant to be. The pair met on the set of the WB drama in 2003 and eventually tied the knot in 2005. After just five months of marriage, the couple announced their separation and then officially divorced one year later. To make matters worse, they continued working together for three more years after the split. Awkward…

Nicole Kidman Lenny Kravitz
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5. Nicole Kidman & Lenny Kravitz

Kidman and Kravitz dated from 2003 to 2005, but it wasn’t until years later that we learned how serious their relationship actually was. After starring in HBO’s Big Little Lies with Kravitz’s daughter, Zoë, Kidman was quoted admitting, “Well, I knew Zoë because I was engaged to her father.” She definitely has a thing for musicians.

Kiera Knightley Jamie Dornan
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6. Keira Knightley & Jamie Dornan

Long before Jamie Dornan was Christian Grey in Fifty Shades of Grey, he was the arm candy of budding Pirates of the Caribbean actress Keira Knightley. In 2003, Knightley and Dornan were hired as models on a photo shoot and instantly hit it off. The pair dated for almost two years before Knightley’s fame became too dominant for Dornan to handle and they threw in the towel.

Rachel Bilson Adam Brody
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7. Rachel Bilson & Adam Brody

Rachel Bilson and Adam Brody starred on Fox’s The O.C. as on-screen couple Summer Roberts and Seth Cohen. During the show’s first season, the pair took their adorable chemistry off-screen and began dating IRL. Sadly, it all became too much for the newly famous duo and, after three years together, they went their separate ways in 2006.

Christina Applegate Brad Pitt
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8. Christina Applegate & Brad Pitt

When Christina Applegate was just 18 years old, she asked 25-year-old heartthrob Brad Pitt to accompany her to the 1989 MTV Movie Awards and famously ditched him mid-awards for another date! To this day, Applegate has yet to reveal the name of the mystery man, but all we can say is, how could you?!

Madonna Tupac
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9. Madonna & Tupac

Three years before Tupac's tragic death in 1996, actress Rosie Perez introduced the rapper to her Madgesty at the Soul Train Music Awards. While it's not clear exactly how long the two were together, we do know the couple had an on-again-off-again relationship leading up to Tupac's imprisonment in early 1995. Shortly after his incarceration, he wrote a jailhouse letter to Madonna, where he detailed surprising insights into their mysterious love affair.

Winona Ryder Johnny Depp
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10. Winona Ryder & Johnny Depp

Can you think of a stranger pairing? Depp and Ryder first crossed paths at the Great Balls of Fire premiere in 1989 and started dating two months after. Cut to five months later, and they were engaged! But, just as all good things come to an end, in 1993, the couple announced they were calling off their engagement, which forced Depp to change his tattoo from “Winona Forever” to “Wino Forever.” We'd totally drink wine with you forever, Johnny. 

Jennifer Aniston Tate Donovan
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11. Jennifer Aniston & Tate Donovan

In 1995, Jennifer Aniston reached the pinnacle of her career playing Rachel Green on Friends. That same year, she fell for The O.C.'s beloved Tate Donovan. The couple had a highly publicized relationship and was briefly engaged until they called things off in 1998, just before a Mr. William Bradley Pitt entered the picture. Awkwardly enough, Aniston and Donovan were forced to remain cordial following their breakup because Donovan was playing Rachel Green's love interest, Joshua Burgin, on Friends at the time. Justin Theroux for the win.

RELATED: 9 O.G. Celeb Couples Who Still Got It Goin’ On

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