Justin Timberlake Was ‘Strict’ With Britney Spears When They Dated, Claims Kathy Griffin

Were things between Britney Spears and then-boyfriend Justin Timberlake a little too toxic?

According to Kathy Griffin, the “Cry Me a River” singer — who dated Spears from 1999 to 2002 — was not that nice to his girlfriend at the time (at least from what the comedian saw).

In a clip posted to Instagram on Tuesday, October 28, promoting this week’s episode of Kathy Griffin: Talk Your Head Off, the My Life on the D-List star recalled the time she wrote “a little sketch where Britney and I were fighting over Justin” for the 1999 Billboard Music Awards.

“What I remember about this was that Britney was such a big star, she couldn’t come to rehearsal, so we had to rehearse for just a couple of minutes right before we went out on live network television,” said Griffin, 64.

“Justin was not totally respectful to Britney during our little rehearsal,” she continued, implying the boy band member, 44, would say things like: “Baby, don’t do it like that. Baby, say it like this. Baby, don’t roll your eyes like that. Baby, don’t walk like that.”

Griffin then said jokingly, “And I was like, ‘Baby, don’t make me hit you one more time.’”

She explained, “I just couldn’t figure out… He was very, let’s just say, strict with her. I actually talk about this, and I talk about the behind-the-scenes of this moment in my special, which you can currently see for free, called Kathy Griffin: My Life on the PTSD List.”

The “Gimme More” singer, 43, dated Timberlake in the late ‘90s and early 2000s. Spears dropped a few bombshells in her 2023 memoir, The Woman in Me, regarding their highly publicized romance — including the fact that she allegedly had an abortion while they were dating.

He publicly apologized to Spears in 2021 for his behavior, saying that he knows he “failed” her.

Earlier this month, a source exclusively told Star that Timberlake has “sympathy towards Britney” following the release of her ex-husband Kevin Federline’s explosive memoir, You Thought You Knew.

Timberlake, said the source, “thinks it’s despicable that Kevin’s hitting her with all these terrible insults and sleazy revelations about their time together while she’s at her lowest.”