Kristin Cavallari, Jay Cutler, Jesse James, Kat Von D, Hugh Hefner, Crystal Harris

Charley Gallay/Getty Images; Chelsea Lauren/WireImage; Kevin Winter/Getty Images

Jesse James and Kat Von D called their whole thing off. Kristin Cavallari and quarterback Jay Cutler did, too.

Looks like it's time—again—to recall the stories of Hollywood's most infamous broken engagements.

The following piece originally ran in August 2010, otherwise Hugh Hefner and Crystal Harris, to name two more recent nuptial-nixers, would've made the cut: 

Julia Roberts, Kiefer Sutherland


1. Julia Roberts and Kiefer Sutherland: Hef can relate, to a point. Twenty years ago, hundreds of A-listers were to gather on a studio lot to witness the celebrity wedding of the year. Then, just three days prior to the big to-do, the future star of Runaway Bride bolted. Unlike in the matter of Hefner and Harris, a third-party stripper reputedly was to blame.

Gwyneth Paltrow, Brad Pitt


2. Gwyneth Paltrow and Brad Pitt: All things considered, the impossibly blonde couple's 1997 un-engagement wasn't especially remarkable, except for one sad coda. At the time they called things off, Paltrow and Pitt were to star in a film for Paltrow's beloved father, Bruce Paltrow. The movie, Duets, got made, but minus Pitt, it bombed. Bruce Paltrow died two years after its release.

Jennifer Lopez, Ben Affleck


3. Jennifer Lopez and Ben Affleck: In the beginning, in 2002, they were cute. By 2003, they were the Gigli-dropping publicity monster known as Bennifer. Then, as their late-summer wedding neared , Affleck made headlines for visiting a strip club and Lopez reportedly wanted to call the whole thing off. But, no! Bennifer would not be stopped! A date was set! Guests were summoned! And, then, a la Roberts and Sutherland, the mission was called off three days prior to launch. The two remained engaged until January 2004, when it was finally all over but the release of Jersey Girl.

Lance Armstrong, Sheryl Crow

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4. Sheryl Crow and Lance Armstrong: She cheered him on. She dedicated an album to him. She waited for his divorce to become final. She posed in a wedding dress for a magazine. She didn't get the ring. Wait?! What?! Yup, the couple called it quits in early 2006. Three weeks later, to add scary disease to insult, she was diagnosed with breast cancer. Ugh.

Katie Holmes, Chris Klein

Jamie McCarthy/WireImage

5. Katie Holmes and Chris Klein: They seemed the perfect match: the Dawson's Creek girl and the American Pie boy. But in March 2005, after five years of coupledom, they announced they'd ended their engagement. If that was all there was to the story, it'd be the end of the story. But there was a kicker, all right. Just about eight weeks after Holmes and Klein broke it off, movie-god Tom Cruise swooped down from Mt. Olympus, and put a rock on Holmes' finger himself.

(Originally published Aug. 10, 2010, at 6:55 p.m. PT)

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