Justin Timberlake Broke Up with Britney Spears in a Two-Word Text Message While Spears Was Shooting a Music Video

Is it Tuesday yet? The more snippets we get of Britney Spears’ forthcoming memoir, The Woman in Me, the more we want our hands on all of its 288 pages. (The book drops on Tuesday, following much anticipation.) Snippets about Spears' life have been plentiful this week, including this one, which is not from Spears’ memoir but from an eyewitness to a pivotal moment in her life: the moment that ex Justin Timberlake—who Spears dated from 1999 to 2002—broke up with her via a two-word text message. (Could it not at least have been three—one for each year?)

Flashback to February 2002: Spears was happy when she stepped on the downtown L.A. set of the music video for her song “Overprotected (Darkchild Remix),” ready to “power through” rigorous dance sessions during a two day shoot, Page Six reports.

“There are those people where there is something inside of them and you don’t know where it comes from—it’s like an ‘X’ factor,” said the video's director Chris Applebaum. “That’s what we saw with her. I was so happy that this person who was the biggest star in the world was everything I wanted her to be and then more.”

Toward the end of the second day, Applebaum said that Spears suddenly went missing for about 20 to 40 minutes—a “long time,” he said, because it costs “20 grand to sit around.” When he arrived at her trailer, he found Spears sitting on the floor in a Juicy Couture sweatsuit (very 2002, indeed) with her legs crossed, makeup smudged, and in tears. She held up her Motorola flip phone to Applebaum (also very 2002) and said, “I can’t believe it. Look it. This happened.” She then showed Applebaum a text from Timberlake that read, simply but profoundly, “It’s over!!!” (Even though there were only two words, at least there were three exclamation points.)

Timberlake had been trying to reach Spears all day while she was at her shoot, Applebaum said, in large part because he was “pissed” about Spears’ infidelity with choreographer Wade Robson, which Spears admitted to in her book. (Timberlake was also unfaithful, Spears writes, cheating on her with “six or seven girls,” and claiming that Timberlake cheated first.) Spears’ longtime assistant and friend Felicia Culotta put her arm around Spears and comforted her; Spears was hesitant to finish the shoot, and Applebaum was sensitive to her, saying, “If you don’t have it in you, I totally understand…but if you want to go out there and finish this last setup in the rain, you can show him that he just made the biggest f—ing mistake of his life.” Spears looked at Applebaum earnestly and said, “You know what? That’s a good idea. I’m going to show him that he blew the best thing he ever had.”

Applebaum said Spears then shot the rest of the video in the rain with even more “conviction,” as if she were “on a mission,” he said. Watch the video for yourself here.

"The Woman in Me" by Britney Spears

After the breakup, Spears fled to her home state of Louisiana, where she felt “comatose”; meanwhile, Timberlake was “happily running around Hollywood,” she writes in The Woman in Me. A few months later, Timberlake’s single “Cry Me a River” was released, vilifying Spears and seemingly confirming that she was unfaithful. Spears writes in her memoir that the song and its accompanying music video, which featured a woman who looked just like her, portrayed her as a “harlot who’d broken the heart of America’s golden boy.”

It was a narrative that was reinforced in a 2003 interview with ABC’s Diane Sawyer, where the veteran journalist asked Spears “You broke his heart, you did something that caused him so much pain, so much suffering…what did you do?” Spears writes in her book that she felt “exploited” by Sawyer, her father Jamie, and her management team, who pushed her to do the interview before she was ready.

In response to “Cry Me a River,” Spears released her own song, “Everytime,” in which she acknowledged her contributions to her and Timberlake’s split. (Watching the music video again, 20 years later, is chilling, especially in light of what we now know via Spears’ tell-all.)

Both Spears and Timberlake rebounded with other celebrities for short-lived flings; Spears had a brief romance with actor Colin Farrell, Access reports, writing in her memoir that they “had a two-week brawl” in 2002 after meeting through a “club promoter friend.” “Brawl is the only word for it,” she writes. “We were all over each other, grappling so passionately it was like we were in a street fight.” The two met right after her split from Timberlake. “As I had before when I’d felt too attached to a man, I tried to convince myself in every way that it was not a big deal, that we were just having fun, that, in this case, I was vulnerable because I wasn’t over Justin yet,” she writes. Spears later joined Farrell at the premiere of his 2003 film The Recruit, where he denied they were in a relationship: “We’re not dating,” he said at the time. “She’s a sweet, sweet girl. There’s nothing going on—just mates.” Of their whirlwind romance, Spears described Farrell as “the cutest, hottest thing in the world,” in her book, Entertainment Tonight reports.

Timberlake eventually married actress Jessica Biel in 2012; Spears married Jason Alexander for just 55 hours in 2004, and later that same year married Kevin Federline, with whom she shares two sons—they divorced in 2007. Most recently, Spears married Sam Asghari in June 2022, and, 14 months later, Asghari filed for divorce this past August.