Hollywood is exceptional in many ways, but it is also quite weird sometimes. Over the years we have seen it produce many unusual couples that just didn’t seem to fit together. Check out some of the weirdest celebrity hook-ups.

Rosario Dawson and Danny Boyle

 

 

 

 

 

 

Rosario Dawson has dated several gorgeous actors and models, so it was a bit surprising when she indulged in a romantic relationship with director Danny Boyle, who is 22 years older than her. After they broke up, Rosario said: “It’s not like we announced our relationship, so it’s not like we’re going to announce our breakup. I love Danny. He’s wonderful and we dated longer than people think we did. I respect Danny‘s privacy, so it’s not something we really talk about.”

Whoopi Goldberg and Ted Danson

 

 

 

 

 

 

Ted Danson met Whoopi Goldberg while they were filming the movie, Made In America, in 1993. The pair had an affair which led to the breakup of Danson’s marriage. “I’d walk in Whoopi’s shadow for the rest of my life–I adore the woman,” Danson said about Goldberg.

Tom Cruise and Cher

 

 

 

 

 

 

Believe it or not, these two were once an item. Back in the mid ’80s and before he became a huge star, Tom and Cher were going strong. “He was so wonderful. And I was so crazy about him,” said the iconic singer in 2008. “And he was so, like, different. He was a shy boy. He didn’t have any money.”

Sandra Bullock and Ryan Gosling

 

 

 

 

 

 

The hunky actor and funny girl were together from 2002 to 2003. “I had two of the greatest girlfriends of all time. I haven’t met anybody who could top them,” Gosling told Us Weekly in 2011 (about Bullock and Rachel McAdams, whom he dated afterward).

Angelina Jolie and Jonny Lee Miller

 

 

 

 

 

 

Before Brad Pitt and even before Billy Bob Thornton came Jonny Lee Miller, Angie’s first husband. The two actors married in 1996, separated in 1997, and divorced in 1999, but are to this day good friends.

Evan Rachel Wood and Marilyn Manson

 

 

 

 

 

 

Evan Rachel Wood and Marilyn Manson started dating in 2007. They battled public opinion but work commitments saw them split in 2008 before reuniting and becoming engaged in January 2010. Their engagement ended in August that year though.

Lisa Kudrow and Conan O’Brien

 

 

 

 

 

 

These two dated when he was a writer for Saturday Night Live and she was working as a comedian in Los Angeles. “He was really smart, really funny and he thought I was funny, but found we were better as friends,” Lisa said of their brief romance.

Sarah Jessica Parker and Robert Downey Jr.

 

 

 

 

 

 

By his own admission, Robert Downey Jr. was less than a model boyfriend to Sarah Jessica Parker, whom he dated from 1984 to 1991. “I liked to drink, and I had a drug problem, and that didn’t jibe with Sarah Jessica, because it is the furthest thing from what she is,” Downey Jr. said of their relationship.

50 Cent and Chelsea Handler

 

 

 

 

 

 

One of the most unexpected hookups was Handler’s short-lived romance with rapper 50 Cent. The two met when he appeared as a guest on her show. The duo were photographed on several dates in 2010. Chelsea has admitted to “casually” dating 50 Cent, though they are no longer together.

Diane Keaton and Al Pacino

 

 

 

 

 

 

Keaton dated her Godfather co-star Al Pacino in the ’80s; the relationship was over after Keaton pushed a marriage ultimatum on Pacino. She told People: “He’s charming, hilarious, a nonstop talker. There was an aspect of him that was like a lost orphan, like this kind of crazy idiot savant. And oh, gorgeous! I was mad for him. I worked hard on that one.”

Mariah Carey and Nick Cannon

 

 

 

 

 

 

Grammy Award-winning singer Mariah Carey and actor, comedian, and rapper Nick Cannon met in 2008 on the set of Mariah’s video for “Bye Bye,” and they married less than three months later. They’re still going strong today and have since become proud parents to twins Moroccan and Monroe.

Mila Kunis and Macaulay Culkin

 

 

 

 

 

 

Though Macaulay and Mila kept their relationship extremely low-profile, the duo were together for over eight years. They were last photographed together at Michael Jackson’s funeral in September 2009, and officially announced their split at the end of 2010.

Edward Norton and Courtney Love

 

 

 

 

 

 

This unlikely couple dated for three years in the ’90s after co-starring in The People vs. Larry Flynt together, and was even rumored to be engaged. Years later, in 2010, Love would blast Norton on Twitter over an alleged $300,000 she said the actor owed her.