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Exes at the Oscars

Celebrity couples are a fickle bunch — and you needn’t look any further for proof. These beautiful, glamorous, and oh-so-in-love pairs celebrated the Academy Awards, Hollywood’s biggest night, arm in arm. However, these images have long outlasted their love stories. In honor of the big show, join us for a trip down memory lane.

Leonardo DiCaprio and Gisele Bündchen, 2005

The only blonde on Leo’s arm come Oscars night this year will be his mom, Irmelin. This is the reason why: Over a decade ago, the Best Actor nominee and his then-squeeze, Gisele Bündchen — who had been dating for over five years at that point — finally made their red carpet debut at the big event. While she looked gorgeous, he looked pretty uncomfortable — and apparently he was. They broke up several months later. Although The Revenant star has romanced no shortage of beauties since (and he’s currently linked to this model), he has never handed out the golden ticket again. It’s either Mama or his vape pen. Sometimes both. (Kevin Mazur/WireImage)

Jennifer Lopez and Ben Affleck, 2003

This photo says everything about Bennifer’s relationship at that point in time — from the fact that he was looking over her shoulder while they kissed to his blotchy spray tan and slicked-back coif. By the following year, the couple only had memories of their time together — and a $2.5 million, 6.1-carat pink diamond engagement ring that he ended up selling. (Dan MacMedan/WireImage)

Cameron Diaz and Matt Dillon, 1998

Yes, they dated. After bonding over hair gel and stuff on the set of There’s Something About Mary, the co-stars embarked on a three-year romance and were each other’s plus-ones. While they looked comfortable together — or maybe it’s just Cameron Diaz’s pajamas?! — they soon outgrew each other, like Cameron outgrew that schoolgirl bob. (Kevin Mazur/WireImage)

Nicole Kidman and Tom Cruise, 2000

A year before their nasty divorce, she was looking at him and he was looking up at… Xenu? (Getty Images)

Alec Baldwin and Kim Basinger, 1991

No, this is not a prom photo. One year after they met and two years before they married, Ireland Baldwin’s parents (Kim, looking like Barbie, and Alec, looking like he needed a shave) attended the show together. (Barry King/WireImage)

Jennifer Aniston and John Mayer, 2009

In hindsight, going to the Oscars together was a bad idea for these two. It was an intense year for Jennifer Aniston — she was a presenter and Brad Pitt and Angelina Jolie were in the audience — so her on-again, off-again beau was there to provide “moral support.” Not enough, apparently, because they broke up just weeks later following a “fight.” (AP Photo/Chris Carlson)

Julia Roberts and Kiefer Sutherland, 1991

Her brassy ‘do was for Hook, and Julia Roberts, who was nominated as Best Actress for Pretty Woman, was hooked on her “beautiful blue-eyed, green-eyed friend” after they co-starred in Flatliners. While you stare at those smiles, remember how things ended: with Julia as a real-life runaway bride! (Vinnie Zuffante/Getty Images)

Johnny Depp and Vanessa Paradis, 2004 

French singer and model Vanessa Paradis helped Johnny Depp, nominated in the Best Actor category for Pirates of the Caribbean: The Curse of the Black Pearl, through what will go down in history as his worst. hair. day. ever. (

Winona Ryder and Christian Slater, 1989 

J.D. and Veronica were really a thing — and serious enough to attend the Oscars together … back when cummerbunds were in. We wonder if people went up to them all night asking, “What’s your damage?” We totally would have. (Ron Galella/WireImage)

Jesse James and Sandra Bullock, 2010

We all remember what happened just weeks after this photo was taken. Out of respect for Sandy, winner of the Best Actress award for The Blind Side and our favorite girl next door, we won’t even rehash it. (Getty Images)

Cindy Crawford and Richard Gere, 1991

The supermodel, who turned 50 this month, was just 25 when she attended the awards with the Pretty Woman actor, who was 17 years her senior. They married later that year (exchanging tinfoil rings!) but didn’t make it through 1994 — despite bizarrely dropping $30,000 on an ad proclaiming they were “heterosexual and monogamous and take our commitment to each other very seriously.” They always seemed like an odd match. (Ron Galella/WireImage)

Robin Wright and Sean Penn, 2009

With their hot-and-cold marriage, we’re surprised they even attended the show together in 2009, when he was named Best Actor for Milk. It’s fitting they both wore black, though, because they somberly ended their marriage — splitting for good — that same year. (Getty Images)

Brad Pitt and Juliette Lewis, 1992

Did he tell her it was a good idea to wear those cornrows? Did she tell him it was cool to wear those shoes? The lovebirds looked more like they were going to a costume party than to the Hollywood party of the year. But who could blame them? At 28 and 18, they were practically babies. (Jim Smeal/WireImage)

Uma Thurman and Ethan Hawke, 2002

Forget Uma, Oprah! It was Uma, Ethan the year he was nominated as Best Supporting Actor for Training Day. And a fun fact for you: She gave birth to their second child, son Roan, just two months before and still looked this good. (Steve Granitz/WireImage)

Demi Moore and Bruce Willis, 1989

What came between these two? Maybe her cape. (Barry King/Getty Images)

Geena Davis and Jeff Goldblum, 1989

Her dress, his hair… If this isn’t the epitome of the 1980s, we don’t know what is. (Barry King/WireImage)

Anne Hathaway and Raffaello Follieri, 2008 

This photo was taken about seven months before Raffaello Follieri pleaded guilty to 14 counts of wire fraud, money laundering, and conspiracy. Needless to say, he wasn’t her date when she won the Best Actress Oscar for Les Misérables in 2013. (Getty Images)

Don Johnson and Melanie Griffith, 1989 

When your date has better hair than you do. Gulp. We’re sure her Oscar nomination for Working Girl softened the blow. (WireImage)

Antonio Banderas and Melanie Griffith, 2005

If at first your relationship doesn’t succeed, try, try again with hubby No. 3. And wear something that’s very low-cut. (Getty Images)

Hilary Swank and Chad Lowe, 2005 

She called him her “everything” in her acceptance speech for Million Dollar Baby. By the next year’s ceremony, she was calling him her ex-husband. (Getty Images)

Halle Berry and Eric Benét, 2002 

The newlyweds were so close that she brought him with her to the press room after she won the Oscar for Monster’s Ball. Weird. By October of that year, she had made him out to be a monster, telling the world he was a sex addict. (Getty Images)

Sarah Larson and George Clooney, 2008

Remember when the Cloonster brought the Las Vegas cocktail waitress to the Oscars? Man, we’d love to hear Amal’s take on that one. (Getty Images)

Ryan Phillippe and Reese Witherspoon, 2006

Why so glum, Ryan? You’d think your husband would be a little more excited for your Oscar win. That wasn’t the case for the Walk the Line star and her Cruel Intentions co-star, who ended their marriage later that year. (Getty Images)

Julia Roberts and Benjamin Bratt, 2001 

We thought the “matching friendship rings” they wore would have kept them together (hehe!), but, alas, the Erin Brockovich actress parted ways with the Law & Order hunk a few months after Oscar came into her life. So it goes. (Getty Images)

Happy Father’s Day to all the badass, the living legends, the shit kickers, and hurricanes of destruction. You did it first, you did it way better than we ever could, and you’re still cooler than we will ever be. 

Grab a copy of Dads are the Original Hipsters for a last minute gift this year.


NEW YORK - JULY 20: Teairra Mari, Jay-Z and Rihanna answer questions at the Shawn “Jay - Z” Carter Hosts Teen People Listening Lounge at the Canal Room on July 20, 2005 in New York City.  (Photo by Brad Barket/Getty Images)