Let's figure out which ex-boyfriend Drew Barrymore once made cry

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Drew Barrymore attends the season premiere of <em>Santa Clarita Diet</em> on March 22 in Los Angeles. (Photo: Presley Ann/Patrick McMullan via Getty Images)
Drew Barrymore attends the season premiere of Santa Clarita Diet on March 22 in Los Angeles. (Photo: Presley Ann/Patrick McMullan via Getty Images)

Drew Barrymore’s appearance on Thursday’s Jimmy Kimmel Live! came with her usual bubbly personality, but there was also a side of mystery.

The Santa Clarita Diet star, 43, told a story about a time that she pulled a Carrie Underwood à la “Before He Cheats” — well, a tamer version — on a former flame. She didn’t explain his offense, but it must have been pretty bad.

I spray-painted an ex-boyfriend’s car,” Barrymore said. “It was really fun. We blasted Cypress Hill. It was mid-’90s, late ’90s. We felt so baller.”

Barrymore and her accomplice, a friend named Justine, attempted to cover their tracks. The actress said she wrote, “a lot of really horrible things that would not seem like me. It wasn’t like, ‘You screwed me over, you d***.’ It was like, ‘Anarchy’ and ‘Black Flag.’ And then he called me crying like a little bitch, and he said, ‘You wouldn’t have done this, would you have?’ And I was like, ‘Noooo.’”

In fact, she said the ex never found out that she was the graffiti artist — until now.

Now, Barrymore has a long list of boyfriends in and out of (but mostly in) the entertainment industry. She’s been a recognizable celebrity and a working actress since she starred in E.T. the Extraterrestrial at age 7; where else was she supposed to meet people? And because most of her relationships have played out in the public eye, these are a few of her former flames who could be the mystery boyfriend from the story Barrymore told.

First off, both David Arquette, whom Barrymore dated for a few months in 1991, and Balthazar Getty, her beau briefly in 1990, can be eliminated. Unless Barrymore’s timeline was seriously off, they dated her too early to be the subjects of her story.

However, there are a few guys we know she dated around the mid- to late ’90s who you might recognize.

Jamie Walters

Barrymore and Jamie Walters at the Hollywood premiere of <em>Poison Ivy</em> on May 4, 1992. (Photo: Ron Galella, Ltd./WireImage)
Barrymore and Jamie Walters at the Hollywood premiere of Poison Ivy on May 4, 1992. (Photo: Ron Galella, Ltd./WireImage)

The “How Do You Talk to an Angel?” singer and actor — remember The Heights? — was with Barrymore in 1992-1993, which might be too early. Still, it wasn’t much earlier and, in May 1993, Barrymore told Seventeen that the breakup was the worst pain she’d ever felt. They were engaged at the time. “Drew says Jamie broke off their engagement by phone three days before she was due to return to their L.A. home (she was in Vancouver filming The Amy Fisher Story),” according to the magazine. “She asked him to wait until they could discuss breaking up in person, but by the time she returned home, Jamie had moved all of his things out.” Ouch. He’s a contender.

Jeremy Thomas

Barrymore and Jeremy Thomas, pictured on April 19, 1994, had a short-lived marriage. (Photo: Barry King/Liaison)
Barrymore and Jeremy Thomas, pictured on April 19, 1994, had a short-lived marriage. (Photo: Barry King/Liaison)

The British bar owner probably isn’t the car guy, simply because he was more than an ex-boyfriend to Barrymore. He was her first husband, married to her for a few weeks in 1994, when she was still a teenager.

Eric Erlandson

Eric Erlandson of Hole accompanied Barrymore at the 1995 debut of her movie <em>Batman Forever</em>.&nbsp;(Photo: KMazur/WireImage)
Eric Erlandson of Hole accompanied Barrymore at the 1995 debut of her movie Batman Forever. (Photo: KMazur/WireImage)

Courtney Love, a close friend of Barrymore’s, introduced her to Erlandson, the guitarist for Love’s band Hole. They dated from 1995 — they were at the June 9 premiere of Batman Forever  together — through the first few months of 1996. An interesting side note: Love herself had a relationship with Erlandson at some point.

Edward Norton

Barrymore and Edward Norton were a thing at the 1999 Oscars. (Photo: Kevin Mazur Archive/WireImage)
Barrymore and Edward Norton were a thing at the 1999 Oscars. (Photo: Kevin Mazur Archive/WireImage)

Barrymore dated Norton for a few months around the time they made the 1997 movie Everyone Says I Love You. Here’s where Barrymore’s friend Love — Barrymore is even godmother to Love’s daughter, Frances Bean Cobain — comes in again. The rocker also reportedly had a romance with Norton around this time when she was making The People vs. Larry Flynt with him. (Love and Norton both denied dating rumors at the time, but she later confirmed that there had been a romance.) For what it’s worth, Barrymore and Love remained friends for at least a few years afterward. They didn’t sound like they were close by 2007, though, when Barrymore told Jane magazine she hadn’t been in Frances’s life for “a few years.” Hmm…

Luke Wilson

Luke Wilson and Barrymore hand-in-hand at the <em>Everyone Says I Love You</em> premiere in New York City. (Photo: Ron Galella/WireImage)
Luke Wilson and Barrymore hand-in-hand at the Everyone Says I Love You premiere in New York City. (Photo: Ron Galella/WireImage)

Barrymore’s leading man in 1998’s Home Fries was her real-life beau too. They ended things the year the movie came out, but they remained on such good terms that she cast him in the Charlie’s Angels reboot that she produced in 2000. It probably wasn’t him.

After the mid- to late ’90s period Barrymore described, she was into comedian Tom Green in what would become her most infamous relationship. Barrymore and Green married in 2001 but didn’t quite make it to their first anniversary before splitting.

She later married and divorced art consultant Will Kopelman. He’s the father of her two daughters, Olive, 5, and Frankie, 4 — the true loves of her life. He probably doesn’t need to worry about his car, unlike maybe Walters did… or maybe Norton.

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