The Top 10 Most Surprising Celebrity Coupling Moments In Recent Memory

Kimberly Stewart and Benecio Del Toro are Hollywood's latest odd couple.

ByABC News
May 29, 2011, 3:52 PM

May 30, 2011 — -- When it comes to covering the loves lives of the rich and famous, there are your expected headlines --like that Justin Timberlake and Jessica Biel broke up after years of speculation that they would. And then there are the headlines that come completely out of the blue.

Take, for example, when we read that Rod Stewart's celebutante daughter, Kimberly Stewart, is pregnant with Benecio Del Toro's baby; all we could think was, "Who? Huh? What?" It's just so … random. Yet, Benecio's rep confirms that it is true. "Although they are not a couple, they are looking forward to the arrival of the baby," she says. Below, more celebrity couple news that left us scratching our heads:

Tom Cruise and Katie Holmes. When Tom Cruise announced in 2005 that he and Katie Holmes were dating, it didn't make a lot of sense. He was an established movie star who's all into Scientology and she was a young "Dawson's Creek" alum who was openly Roman Catholic. Two months later they got engaged. The rest, as they say, is very random history.

Natalie Portman and Benjamin Millepied. We knew Natalie Portman was very happy with her dancer boyfriend, Benjamin Millepied, who she met him on the set of "Black Swan." But when her rep announced in late December that she was preggers and engaged, we were sideswiped.

Ellen DeGeneres and Portia de Rossi. In 2005, to our knowledge, Portia de Rossi was straight. And then all of a sudden, she was dating Ellen DeGeneres. Turns out, the two are totally adorable and got married three years later.

Demi Moore and Ashton Kutcher. In 2003, we were surprised enough to see Demi Moore re-emerge in "Charlie's Angels: Full Throttle" in a tiny bikini. When she started dating Ashton Kutcher -- 15 years her junior -- we were very confused.

Scarlett Johansson and Sean Penn. Speaking of unlikely age differences, when Scarlett Johansson split from husband Ryan Reynolds, we never imagined that she'd end up with Sean Penn, who is twice her age -- but it's happening right before our eyes.

Evan Rachel Wood and Marilyn Manson. We thought Evan Rachel Wood was that sweet girl from "Once and Again" -- until she appeared in Marilyn Manson's video for "Heart Shaped Glasses." The two were an out-of-nowhere couple.

Taylor Swift and Jake Gyllenhaal. Another head scratcher. Earlier this year, we didn't believe it for a second when we heard that Jake Gyllenhaal and Taylor Swift were dating. In addition to an age difference -- not to mention a genre and city difference -- they just seem like such opposite types of people.

January Jones and Bobby Flay. In June, January Jones' car hit three parked vehicles. Who did she call for assistance? Bobby Flay. Which lead many to think that the two were having an affair.

Michael Jackson and Lisa Marie Presley. Perhaps the biggest seemingly crazy couple in recent memory -- when Lisa Marie Presley, daughter of the King, married Michael Jackson, the King of Pop, just 20 days after getting divorced.