Christina Applegate Ditched Brad Pitt at the 1989 VMAs for a Gilmore Girls Star

Who

Emmy winner and three-time Golden Globe-nominated actress Christina Applegate, 50, and actor and Oscar-winning producer Brad Pitt, 58.

How They Met

Christina, born to actress Nancy Priddy and record producer Robert Applegate, once shared that as a teen starring in Married … with Children, Brad Pitt and Jason Priestly would come over for barbecues. It's unclear whether Pitt previously knew the family or if it was through Christina that he scored the invite (they both guest-starred in 1988 episodes of 21 Jump Street), but either way, to be a fly on that retro grill …

When They Peaked

Like true love-struck teens, Applegate, her teased hair, and Pitt, with his discolored leather jacket, decided to tango for a photographer during a 1988 photo op. Can you imagine Brad sweeping Angie up in a silly red carpet waltz? New and unaffected fame is the best kind.

Why We Loved Them

As mentioned above, Christina and Brad were really just kids when they got together. Pitt's Hollywood reign was a ways off — just one year ahead of his and Applegate's picture-perfect tango; he'd been featured as uncredited "Boy at the Beach" in a movie called Hunk. Both on the cusp of superstardom, we imagine it was an exciting time.

The Breakup

During a 2015 appearance on Watch What Happens Live, Applegate admitted to host Andy Cohen that the rumors were true: she'd ditched Brad Pitt the night of the 1989 MTV Video Music Awards for another man.

You didn't misread that: Christina Applegate ditched 26-year-old Brad Pitt — puppy dog eyes, endearingly greasy '80s hair, and all — for someone else. Who could possibly hold a candle to young Brad Pitt, you ask? Well, the Dead to Me star wasn't eager to share, noting only that the man in question wasn't an actor but was known to the public.

However, Applegate's co-conspirator wasn't quite as shy. Skid Row singer and Gilmore Girls star (Gil!) Sebastian Bach came forward a year later, claiming to be the mystery man.

While promoting his memoir 18 and Life on Skid Row on the radio show Elliot in the Morning, he reportedly spoke of the pair's "brief fling," explaining, "[Christina] was interviewed recently on, like, Entertainment Tonight, or something, and they said, 'What was the dumbest thing you ever did?' And she goes, 'One night I ditched Brad Pitt for this other dude.' And that dude would be me. So there was a time on this earth when Sebastian Bach was, like, a hotter lay than Brad Pitt."

For reference, this is what Bach looked like in 1989:

Applegate has never confirmed that Bach is the man who came between her and Pitt. And though she and Pitt never dated again following the VMAs, they have seen each other in the years since — so the wounds have seemingly healed. That same year Brad was linked to Pee-Wee's Big Adventure star, E.G. Daily, so he probably wasn't too broken up about it.

Where They Are Now

Where to begin … Pitt went on to date the bulk of single '90s-era actresses in Hollywood, including Kalifornia co-star Juliette Lewis and Gwyneth Paltrow (to whom he was briefly engaged). The Ocean's Eleven stars wed Jennifer Aniston (whose big sister on Friends was played by Applegate, coincidentally) in 2000. They famously sparked a media firestorm when he and Angelina Jolie began publicly dating soon after his and Aniston's 2005 split. Pitt and Jolie shocked the world with their separation in 2016 — they share six children together (Maddox, 21, Pax, 18, Zahara, 17, Shiloh, 16, and 14-year-old twins Knox and Vivienne). In the years since, there's been much speculation regarding his dating life (Charlize Theron and MIT professor Neri Oxman among the rumored romances), but nothing has been confirmed.

Yes, it's the leg that launched a thousand memes, but it's also the duo that seemed to set the Hollywood It Couple mold back in the day. Seemingly perfect in every way, the couple soon called it quits, but every time any other actor flashes a leg, Jolie gets all the credit.

Pitt's production company, Plan B Entertainment, has several high-profile projects, including The Departed, 12 Years a Slave, and Moonlight, which each won a Best Picture Oscar. The veteran actor starred in Quentin Tarantino's 1969-set ode to the film industry, Once Upon a Time in Hollywood. Pitts more recent film credits include Bullet Train, The Lost City, and Babylon.

Applegate wed actor Johnathon Schaech in 2001 and filed for divorce in late 2005. In 2013, she married Porno for Pyros bassist Martyn LeNoble, with whom she welcomed daughter Sadie Grace in 2011.

The inspiring actress, who is a breast cancer survivor recently diagnosed with multiple sclerosis, stars in the acclaimed Netflix series Dead to Me alongside Linda Cardellini.

#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.