1. Roger Ebert and Oprah Winfrey
When: The 80s, when lots of wild things like that were happening. Ebert convinced Oprah to syndicate her show, because of the success he had with Sneak Previews. So, without Roger Ebert, there would be no Oprah. He, like, invented her.
Status: Oprah’s engaged in her Steadman-Gayle love triangle, and Ebert’s married to Chaz, who has a bit of an Oprah thing going on. Meaning that Ebert has a type, and it’s Oprah.
2. Barbara Hershey and Sayid from Lost
When: They started dating in 1998, despite their twenty-one year age difference and the fact that Barbara Hershey kind of scares me. (Can’t you just see her quoting lines from Black Swan to him?)
Status: Broken up, as of 2010.
3. Jack Nicholson and Lara Flynn Boyle
When: Together off and on throughout the 90s, and Lara compared dating him to “being with the king.” I guess she hasn’t seen The Shining.
Status: No longer a thing, although rumors sparked up in 2006 that the two were again an item. I still find it weird.
4. Michael Jackson and Brooke Shields
When: That time that hell froze over and chaos reigned.
Status: No longer together, for numerous (and obvious) reasons.
5. Nicolas Cage and Brooke Shields
When: Cage is an immortal, so he’s probably dated a lot of people. He briefly dated Shields in the 80s, who he attended the premiere of Moonstruck with. He was kind of normal then, so cut Shields some slack for this one.
Status: Cage has been married to Alice Kim since 2004 and Shields to Chris Henchy since ’01.
6. Natalie Portman and Moby
When: Moby mentioned his brief dalliance with dating Natalie Portman during an interview with Spin in 2008 and confessed that “dating Luke Skywalker’s mom” made him “the target of a lot of nerd wrath.” Perhaps it was also because after Play, all of his other albums sucked. #justsaying
Status: After doing it with Devendra Banhart for awhile, Portman married her Black Swan co-star, Benjamin Millepied. Moby is busy not living up to his potential.
7. Rosie Perez and Tupac (#stillalive)
When: This one is technically debatable. Although Perez denies that the two were involved, the two were very, very close throughout the 90’s and attended the 1993 Soul Train Awards canoodling and holding hands. I’ll give Perez the benefit of a doubt (because I’m obsessed with her), but the pictures don’t lie.
Status: The internet says Rosie Perez is single, so you should get at that ASAP.
8. Anne Heche and Steve Martin
When: From 1993-1995, before Heche got involved with Ellen and looked for a spaceship in Fresno, which is (oddly enough) one of the few things she won’t find there.
Status: No longer together, because Anne Heche is a total basket case. (Ellen also traded way, way up.)
9. Edward Norton and Courtney Love
When: They met while filming The People Vs. Larry Flynt in 1996, the movie that proved Courtney Love is a strangely good actress. (She even won a Globe for it, but got snubbed for dat Oscar.)
Status: Separated, because Courtney Love is busy having a two-decade-long public meltdown. (She’s like the Lindsay Lohan that never gets better.) Recently, she has taken to attacking Norton on Twitter, her preferred form of communication with the world.
10. Steve Coogan and Courtney Love
When: Until 2004, when Steve Coogan came to his senses. Love would claim a year later that Coogan was the father of her baby, because she hadn’t slept with another man in the year since they broke up. She would later would blame him for Owen Wilson’s drug problem and “overdose” and took credit for “making him cool.” After making these statements, she ripped open a bag of bread with her teeth and kicked over a microphone, which is how Courtney shakes hands. In other news, Courtney Love is my spirit animal.
Status: God only knows. With Courtney Love, you can never be sure of anything.
11. Ryan Gosling and Sandra Bullock
When: They started dating around the time of filming 2002’s Murder By Numbers. Bullock’s friend Hugh Grant often referred to Bullock’s boyfriend as “The Child,” because he was 16 years younger than Sandra.
Status: Gosling is now with Eva Mendez (lucky witch) and refers to Bullock and Rachel McAdams as the “best girlfriends ever.” Marry me, please.
12. P. Diddy and Cameron Diaz
When: They didn’t date “exclusively” but started hooking up after her breakup with A-Rod in 2011.
Status: Rebound over. P. Diddy is too busy changing his name all the time to be dating anyone. (Is that even his name now? I can’t keep up.)
13. Robbie Williams and Cameron Diaz
When: They reportedly dated in 2003, while engaging in a bout of go-karting and beach hand-holding. (Doesn’t dating Cameron Diaz sound fun?)
Status: The pair never confirmed separating or dating in the first place (blasted privacy!) but are still friends. Diaz even attended Williams’ wedding in 2010, because that sounds like something she would do.
14. Tila Tequila and Billy Corgan
When: Skipping this. I don’t even want to think about it.
Status: I don’t know. Has Tila Tequila been devoured in the Zombie Apocalypse yet? I haven’t checked.
15. Jessica Simpson and Billy Corgan
When: 2009-2010, before Simpson met Eric Johnson and became the pregnant-est person in the history of man.
Status: Separated, probably because what the heck would they talk about in the first place?
16. Tom Cruise and Sofia Vergara
When: Before dating Katie Holmes in 2007, Cruise reportedly “wanted to marry” Sofia Vergara after being introduced to her by mutual friend Will Smith at a party. This is because he’s a human who has eyes.
Status: Vergara dumped him because of his insistence that she would have to convert to Scientology if they got hitched. Not great first date conversation, Tom.
17. Tom Cruise and Cher
When: They met when she was 39 and he was 23, despite their age difference and difference in sexuality. They had a brief affair in 1985, two years before she filmed Moonstruck. Which is great, because had Cher taken Cruise to the premiere to double date with Nicolas Cage and Brooke Shields, the world may have imploded.
Status: Despite being “crazy about him,” the affair ended because of their conflicting film schedules. Cher has never stopped dating younger men. Get it, gurl.
18. John Stamos and Marlee Matlin
When: The two dated in 1989, routinely spotted holding hands and attending red carpet events together. This was after Matlin dated her Children of a Lesser God co-star, William Hurt. Lesson: Marlee got game.
Status: Separated, sadly. Because wouldn’t they have had gorgeous children?
19. Christina Hendricks and Geoffrey Arend
When: When God decided to punish everyone who isn’t Geoffrey Arend. (Seriously. Google a picture of him.)
Status: Married now. Hendricks calls Arend the “best husband ever.” I’m going to go brood now.
20. Teri Hatcher and Michael Bolton
When: Bolton dated Hatcher in the early 90s after she appeared in the video for “Missing You Now” and both of them were still relevant.
Status: Separated. Although Bolton would later go onto date Nicolette Sheridan until they broke up in 2008, who was Hatcher’s co-star on Desperate Housewives. As the other cast members reportedly hated Sheridan, this could not have helped matters much.
21. Matt Damon and Winona Ryder
When: They were Hollywood’s “It Couple” for a hot minute before breaking up in 2000.
Status: After their breakup, Ryder has had a tempestuous relationship with her ex and mutual friend Gwyneth Paltrow, who Paltrow calls “her worst frenemy.” Because if Hollywood were Mean Girls, Gywneth Paltrow would be Regina George.
22. David Duchovny and Winona Ryder
When: Duchovny and Ryder dated in 1996, although the private David Duchovny refuses to talk about it now, saying that they were “just friends.”
Status: Ryder is now stalking Natalie Portman to get her role in Swan Lake (and her pink shirt) back, because movies are real life, and Duchovny is married to (but currently separated from) the forever-hot Tea Leoni.
23. P.T. Anderson and Maya Rudolph
When: P.T. Anderson started dating Rudolph in 2001 circa splitting from Fiona Apple and making Magnolia, becoming my personal favorite celebrity couple. (I need something to get me through the Will Arnett-Amy Poehler divorce.)
Status: Still going strong, because LOVE IS REAL.
24. Dolph Lundgren and Grace Jones
When: They started dating in 1985, after filming A View to a Kill together, which sadly stands as one of the more poorly received Bond entries. (They can’t all be Skyfall.)
Status: No longer a thing, which saddens me, because they’re so weird that they make sense together. Especially when you picture those cheekbones paired up. (So much jawline in one relationship.)
Miscellaneous fact: Did you know Dolph Lundgren is a Fulbright scholar? Weird.
25. Russell Brand and Ginger Spice
When: Following the lead of Eddie Murphy, who got that Scary Spice action for some time, Russell Brand reportedly hooked up with Ginger Spice during this year’s Olympics.
Status: No information, although they never made it press official. Considering that he was married to Katy Perry and then dated Isabella Brewster for a combined two seconds, I assume they are no longer doing it.
26. Ted Danson and Whoopi Goldberg
When: Ted Danson had an affair on his wife with Whoopi Goldberg (???), leading to the end of his marriage to Casey Coates in 1993. Ted Danson’s divorce from Coates, then his second wife, ended up being one of the more costly splits on record. Casey Coates would be awarded $30 million dollars for Danson’s infidelity.
Status: Danson is now married to Mary Steenburgen (who are incredibly cute together) and Whoopi Goldberg became a celestial being that transcends sex and eyebrows.
27. Brad Pitt and Robin Givens
When: Brad Pitt and Robin Givens started dating after her split from Mike Tyson in 1989, after Givens alleged abuse from Mike Tyson. (The pair even alluded to it in a Barbara Walters interview.) Seeing Pitt and Givens together made Tyson very jealous, and he started in an interview that he only recently forgave Brad Pitt for it, not that it was much of his business in the first place.
Status: As Pitt has been in the tabloids for relationships with Gwyneth Paltrow, Jennifer Aniston and Angelina Jolie for a decade and a half, they’re obviously no longer together.
28. Matthew Perry and Lizzy Caplan
When: They’ve been in a relationship since 2006, after Perry wrapped Friends and Caplan was coming off of Mean Girls.
Status: Still together and still weird. I’ve brought this up before, but it bears repeating because CHANDLER BING AND JANIS IAN HAVE SEX AND I DON’T KNOW HOW TO PROCESS THAT.
29. Lance Bass and Danielle Fischel
When: Bass and Topanga dated from 1999 to 2000, in their Boy Meets World and *NSYNC days. They reportedly never had sex, because obviously.
Status: As Lance is all aboard the man train now, this is no longer a thing. Fischel claims that she had “no idea” Bass was gay. I guess she never watched the “(God Must Have Spent) A Little More Time on You” video.
30. Justin Timberlake and Fergie
When: The former Mickey Mouse Club and Kids Inc. stars started dating in 1997, when he was 16 and she was 23. (Cougar alert!) She admits to regretting it now, because of the age difference. Apparently her friends nicknamed her “Stella” because of the romance, as in Angela Bassett from Stella Got Her Groove Back. (I hope you know what that is, or I’m going to feel old.)
Status: Timberlake recently married Jessica Biel, which broke the internet’s heart. At least we still have J.C.?
31. Kelly Preston and George Clooney
When: This was before Preston married John Travolta, which now makes me think that George Clooney might be gay. (If there is a God.)
Status: Clooney will be forever a bachelor, and Preston seems to be happy being a Scientology bride. All of that Grease and Saturday Night Fever money I’m sure helps matters a lot.
32. Martha Plimpton and River Phoenix
When: Phoenix and Plimpton met in 1986 and would date for three years, filming Running on Empty while still a real-life couple.
Status: They broke up in 1989, before Phoenix’ untimely death in 1993.
33. Johnny Depp and Ellen Barkin
When: The nine-years-older Ellen Barkin nabbed the then 31-year-old hunk in 1994, as Ellen Barkin’s hotness defies age. They probably had the sexiest sex in recorded history. (Watch The Big Easy and tell me that’s not accurate.)
Status: They are no longer together, but neither is currently married to anyone else. So… Barkin’s still good to go whenever you are, Johnny.
34. Alanis Morrisette and Dave Coulier
When: This is one I hope you already know about, because it’s awesome. Morrisette dated Coulier in the early 1990s, when she was an up-and-coming singer and he starred as Uncle Joey on Full House.
Status: It didn’t work out, which led Alanis Morrisette to famously write the scorned woman anthem “You Oughta Know” about him. (It’s too bad Full House ended in 1995, because that would have made a great theme song.) Alanis would later go onto date Ryan Reynolds for four years, which just makes me happy. Reynolds is married to Blake Lively now, and Alanis seems to have taken that one much better.
35. Taran Killam and Cobie Smulders
When: After a long three-year engagement, Killam and Smulders wed this September, and SNL and How I Met Your Mother fans everywhere watched their hearts grow three sizes.
Status: Still together. How much would you want to double date with these two?
36. Drew Barrymore and Corey Feldman
When: 1989, briefly.
Status: They broke up, and Barrymore went onto Tom Green, Edward Norton, Fab Moretti of The Strokes and Justin Long, showing that her relationship choices have no clear through line. (Calculate it, internet!) Feldman’s dating status is unclear, which is for the best, because anyone dating Corey Feldman is just weird.
37. Flava Flav and Brigitte Nielsen
When: Nielsen started dating Flav in 2005, which may rank as the most unlikely celebrity pairing of all-time. (Although Renee Zellweger/Jack White and Chelsea Handler/50 Cent are also on my list.) Their relationship was recorded for posterity on the VH1 reality show, Strange Love, and Nielsen would make guest appearances on Flavor of Love, to show the girls what they had to compete with.
Status: They are no longer dating, and it’s better this way. Because otherwise, I never would have gotten to see someone pee on a mansion floor in Flavor of Love 2.
38. Jay-Z and Rosario Dawson
When: Rosario Dawson dated HOVA while she was still a teenager. I hope this wasn’t after Jay-Z saw Kids, because that would just be weird.
Status: Jay-Z traded up by marrying Beyonce, who runs the world. I’m still convinced their child might be Jesus — sent to Earth to battle any Anti-Christ children Kanye West and Kim Kardashian may create.
39. Scarlett Johansson and Benicio Del Toro
Status: The two may or may not have hooked up in an elevator at the Chateau Marmont after the 2004 Oscars, as goes a widely, widely circulated rumor. Although Johansson denies it, Del Toro’s response was more colorful:
“Did I ever have sex in an elevator with Scarlett Johansson after an awards show? I kind of like, you know, I, well. I don’t know. Let’s leave that to somebody’s imagination. Let’s not promote it. I’m sure it has happened before. It might not be the last time either.”
I don’t know what that means, but it’s certainly not no.
Status: Scarlett Johansson is allegedly shacking up with Leonardo DiCaprio, who seems determined to date every blond woman in existence. If those rumors turn out to be true, Blake Lively, Scarlett Johansson, Leonardo DiCaprio and Ryan Reynolds are like the human equivalent of musical chairs. And Benicio is probably still in the Marmont elevator.
40. David Cross and Amber Tamblyn
When: Joan of Arcadia and Tobias Funke have been dating since 2008, when Joan saw Tobias at a party and demanded to meet him, so he could be her “Discipline Daddy.”
Status: Married, as of October. One can only hope they were wearing matching jean shorts under their wedding attire.
41. Sarah Jessica Parker and Robert Downey Jr.
When: Parker and Downey dated from 1984 to 1991, meaning they dated from most of the entire decade of the 80s. Parker stayed with him, despite his drug addiction, saying that she “thought [she] could save him.”
Status: Broken up. Interestingly, Parker also dated Michael J. Fox (while filming Mars Attacks), JFK Jr. and Nicolas Cage, before marrying Matthew Broderick.
42. Tyra Banks and Will Smith
When: Banks and The Fresh Prince dated after playing the objection of his affections, Jackie, in seven episodes of Smith’s hit show in 1993.
Status: The two only dated for a year, and Smith’s next girlfriend was Jada Pinkett, who he would marry. Will and Jada have been together ever since, populating the world with tiny, multi-talented children who whip their hair copiously.
43. Naomi Campbell and Leonardo DiCaprio
When: Campbell and DiCaprio started dating after Titanic was released, at the height of the DiCaprio phenomenon. This was also before Campbell learned that cellphones could used as weaponry, like Chinese daggers you can make calls on.
Status: The two broke up, and DiCaprio would console himself by dating almost every other member Campbell’s posse in the next decade or so, including Kate Moss, Bar Rafaeli and Gisele Bundchen. Leo, you’re such a skeeze.
44. Reese Witherspoon and Stephen Dorff
When: Although Reese was once quoted as saying that she wouldn’t date Dorff for “all the money in the world,” it didn’t take all the money for them to start dating in 1994.
Status: Split. Witherspoon went onto later date Ryan Phillippe, showing she never lost her taste for bad boys.
45. Sofia Coppola and Keanu Reeves
When: While he was filming Dracula, which her father directed.
Status: She later made fun of him in Lost in Translation, so I’m guessing dating Keanu wasn’t a great experience for her. Coppola’s now moved onto being America’s favorite hapless indie muse, marrying director Spike Jonze and Thomas Mars (lead singer of Phoenix) and remaning wistfully melancholic about it all.