Music video director Chris Applebaum has detailed the experience of Britney Spears receiving a breakup text from Justin Timberlake while filming the music video for the remix of her 2002 song “Overprotected.” Applebaum recounted the incident on the podcast “Hyperfixated with Joseph Shepherd,” explaining that the text arrived late into the second day of shooting.
Filming took place in a downtown Los Angeles alleyway, where the production team encountered challenges from residents throwing canned goods onto the set. Applebaum stated that his producer would give $100 bills to the residents to de-escalate the situation, as they wanted to avoid distressing Spears.
As the crew prepared for a final rain sequence, Applebaum could not locate Spears. After a period of searching, he went to her trailer. On his way, Spears' choreographer, Brian Friedman, advised him to stay away, describing the situation as "bad."
Upon entering the trailer, Applebaum found Spears and her team appearing somber. When he asked what had happened, Spears showed him a text message from Timberlake on her flip phone stating that they should "end the relationship."
Applebaum offered Spears the option to stop filming. However, seeing her animal crackers in the trailer reportedly inspired him to encourage her to continue. He suggested she deliver a performance so powerful it would demonstrate to Timberlake what he was losing. According to Applebaum, Spears agreed, saying, "That’s it! You’re right! Let’s do that."
Spears confirmed in her 2023 memoir, “The Woman in Me,” that Timberlake ended their three-year relationship via text message. She wrote that the message from the *NSYNC singer was a simple, "It’s over."
Spears and Timberlake dated from 1999 to 2002.