6 times Justin Timberlake shaded his ex Britney Spears

Here's a sneak peek of the times Justin Timberlake seemingly shaded Britney Spears after their romance fell apart

PUBLISHED OCT 28, 2023

Justin Timberlake and Britney Spears were the 'It couple' of the '90s until their breakup in 2002 (Getty Images)

All the times Justin Timberlake shaded his ex Britney Spears

Justin Timberlake (Getty Image) — Britney Spears and Justin Timberlake were the '90s 'It couple' (Getty Images)

Justin Timberlake and Britney Spears, who first met as child stars in Disney's 'Mickey Mouse Club,' soon became the 'It couple' of the '90s, until their breakup in 2002. Recently, Timberlake has been in the spotlight again after the release of Spears' memoir 'The Woman in Me,' reigniting interest in their tumultuous past. Let's take a closer look at the times the 'Mirrors' singer seemingly shaded the 'Gimme More' pop sensation.

Justin Timberlake's brutal two-word breakup message

Britney Spears and boyfriend Justin Timberlake arrive at the premiere of her movie — Britney Spears and Justin Timberlake ended their relationship in 2002 (Getty Images)

Spears revealed that their relationship ended in March 2002 with a heartbreaking twist after Justin reportedly dumped her through a cold and concise two-word text message. She received this message while filming the music video for 'Overprotected' and it simply read, "It's over!!"

Britney Spears lookalike in 'Cry Me a River video'

Justin Timberlake and Britney Spears at 'A Family Celebration 2001' at the Regent Beverly Wilshire — Justin Timberlake reportedly cast a Britney Spears lookalike in his hit single (Getty Images)

One of the most infamous incidents was the release of Justin's second solo single, 'Cry Me a River.' The music video featured a Spears lookalike, a move that seemed to suggest that Justin was taking a not-so-subtle jab at his ex-girlfriend. The song's lyrics revolved around discovering a partner's infidelity, sparking further controversy and speculation.

Justin Timberlake cheated on Britney Spears

Nicole Appleton attends Magic At The Musicals 2023 at Royal Albert Hall on May 14, 2023 in London, England. (Photo by John Phillips/Getty Images) — Nicole Appleton made headlines in 2000 when she was photographed on a night out with Justin Timberlake (Getty Images)

In Spears' memoir, she accuses Justin of cheating on her with "another celebrity," but does not disclose any names. However, in the year 2000, Justin was notably observed in the company of Nicole Appleton from All Saints. While Spears herself admitted to infidelity during their relationship, these allegations further fueled the public's perception of Justin's actions during their time together.

'Madonna wannabe'

NEW YORK - AUGUST 28: (U.S. TABLOIDS OUT) Britney Spears(L) , Madonna, and Christina Aguilera perfo — Britney Spears and Madonna kiss at the 2003 MTV VMAs (Getty Images)

During the 23rd Annual Rock and Roll Hall of Fame Induction Ceremony, Justin delivered a speech inducting Madonna. In what appeared to be a thinly veiled dig at Spears, he referred to having dated a "Madonna wannabe" in the past. Many interpreted this comment as a direct reference to his former flame.

Justin Timberlake publicly discredits Britney Spears' virginity pledge

400787 05: Musical artists Justin Timberlake (L) and girlfriend Britney Spears (R) attend the premie — Justin Timberlake allegedly made fun of Britney Spears's virginity pledge on 'SNL' (Getty Images)

During their relationship, both Justin and Spears publicly proclaimed their intent to remain virgins until marriage. However, in subsequent years, Justin openly admitted to their intimate relationship. In a 'Saturday Night Live' sketch, he joked, "Publicly they'll claim to be virgins, but privately, he'll hit it."

Justin Timberlake mocks Britney Spears' mental health struggles

In 2007, during a concert, Spears was undergoing treatment for her mental health and addiction issues. Justin, seemingly taking a jab at her indirectly, incorporated the chorus of Amy Winehouse's hit 'Rehab' into his performance of 'Cry Me a River.' This action raised eyebrows and sparked controversy, as many saw it as an insensitive response to the 'Toxic' singer's struggles.