Britney Spears' Music Video Director Recalls 'Solemn' Day Justin Timberlake Sent Her Breakup Text on Set: 'Messed Up the Best Thing He’s Ever Had'

Music video director Chris Applebaum recently opened up about the moment one of the most beloved celebrity romances came to an abrupt end.

Applebaum, who directed Britney Spears' 2002 music video for the Darkchild remix of "Overprotected," shared details about the breakup text she received from Justin Timberlake and the aftermath while on set over 20 years ago.

On the Wednesday, August 5, episode of the "Hyperfixated With Joseph Shepherd" podcast, Applebaum recalled, "It was toward the end of the second day. We were in, like, hour 20 or something like that."

He continued, "We were doing that last rain sequence. We were waiting, and we were all set up, and I didn’t know where she [Spears] was."

"Everyone’s like, 'We’ve been asking. We’ve been knocking on the door. She’s not coming out,'" he added. "Time passed, and I’m like, 'How are we going to get this done?'"

"Finally, I was like, 'OK, I’m going to go and f------ get Britney myself out of the trailer,'" Applebaum, 56, confessed.

He remembered running into Spears' choreographer, Brian Friedman, on his way there. At the time, Friedman warned him to "get away" because it was a "bad situation...something really bad just happened."

"I walked in and Britney was there. And I was like, 'Is everything OK?' And everyone’s solemn and … they have iron curtain eyes. They’re really dark," he continued.

After asking the pop star, now 44, what happened, she showed him her flip phone screen with a text from her "boyfriend" for them to "end the relationship."

Applebaum told Spears, "I feel so bad for you. I feel so sorry," before telling her he would understand if she wanted to stop the shoot, but as he went to leave her trailer, he saw the "Circus" singer's animal crackers, which suddenly "inspired" him.

"The other thing you could do … you could get back out there and do a performance that’s so hot that you show him that he just lost — he just messed up the best thing he’s ever had," he told the Grammy winner.

Having what he described as a "lightbulb" moment, "She … was like, 'That’s it! You’re right! Let’s do that.'"

"And she came out, and that’s why that performance was so cool," he concluded.

Spears and Timberlake dated from 1999 to 2002 after first meeting as kids on The All-New Mickey Mouse Club.

In her 2023 memoir The Woman in Me, she confirmed the *NSYNC alum dumped her over text with two words: "It's over."