The Messiest Celebrity Romantic Affairs Over the Years

The Messiest Celebrity Romantic Affairs Over the Years

These are the affairs that got everyone talking and gossiping.

We may earn a commission from links on this page.
Image for article titled The Messiest Celebrity Romantic Affairs Over the Years
Photo: Dia Dipasupil (Getty Images)

Ever since Good Morning America anchors TJ Holmes and Amy Robach were caught having an affair, they have been the talk of social media. With this scandal at the top of everyone’s mind, The Root decided to take a look back at some of the messiest celebrity romantic affairs over the years.

Advertisement

2 / 17

TJ Holmes & Amy Robach

TJ Holmes & Amy Robach

Image for article titled The Messiest Celebrity Romantic Affairs Over the Years
Photo: Paula Lobo/ABC (Getty Images)

Obviously, we had to start with the most recent scandal. The two GMA anchors always had amazing chemistry while on live television. But many had no idea it would turn into a romantic affair between the two. ABC is investigating Holmes for his relationship with Roback and potentially other colleagues.

Advertisement

3 / 17

Ime Udoka & Nia Long

Ime Udoka & Nia Long

Image for article titled The Messiest Celebrity Romantic Affairs Over the Years
Photo: Randy Shropshire/WireImage (Getty Images)

This scandal shocked the entertainment and sports world. In September, Ime Udoka, head coach of the Boston Celtics, was suspended for a year for having a consensual relationship with a woman who is a part of the Celtics’ staff. This ultimately led to Nia Long and Udoka splitting after a 13-year relationship.

Advertisement

4 / 17

Jada Smith & August Alsina

Jada Smith & August Alsina

Image for article titled The Messiest Celebrity Romantic Affairs Over the Years
Photo: Paras Griffin (Getty Images)

How could we forget the “Entanglement” that was Jada Smith and August Alsina? During a random sit-down with Angela Yee, August Alsina claimed that he had an intimate relationship with Will Smith’s wife, Jada Pinkett Smith. Will and Jada eventually addressed the relationship during an infamous episode of Red Table Talk and explained that the two were separated when Jada was with August.

Advertisement

5 / 17

Tristan Thompson & Khloe Kardashian

Tristan Thompson & Khloe Kardashian

Image for article titled The Messiest Celebrity Romantic Affairs Over the Years
Photo: Jerritt Clark (Getty Images)

I don’t even have enough fingers on my hands to count the number of times Tristan Thompson has allegedly cheated on his longtime girlfriend Khloe Kardashian. The most infamous incident was when he cheated on Khloe with Kylie Jenner’s longtime friend, Jordyn Woods. During an episode of Red Table Talk, Jordyn revealed that Tristan kissed her. This essentially ended her friendship with Kylie and the positive relationship she had with the Kardashians.

Advertisement

6 / 17

Tiger Woods & Elin Nordegren

Tiger Woods & Elin Nordegren

Image for article titled The Messiest Celebrity Romantic Affairs Over the Years
Photo: David Cannon (Getty Images)

Tiger and Elin were married from 2004 to 2010. What ultimately led to them divorcing was that Tiger reportedly confessed to sleeping with 120 other women while the two were married.

Advertisement

7 / 17

Jay-Z & “Becky With the Good Hair” 

Jay-Z & “Becky With the Good Hair” 

Image for article titled The Messiest Celebrity Romantic Affairs Over the Years
Photo: Mike Coppola (Getty Images)

In 2013, rumors came out that the legendary Brooklyn rapper cheated on Beyoncé. Those rumors gained some validity when Bey’s sister, Solange, went at Jay during the infamous elevator incident. On Beyonce’s classic 2016 album, Lemonade, she made multiple references that she was being cheated on. On Jay-Z’s 2017 album, 4:44, Jay-Z seemingly admits to cheating on his wife with “Becky with the good hair.”

Advertisement

8 / 17

Wendy Williams & Kevin Hunter

Wendy Williams & Kevin Hunter

Image for article titled The Messiest Celebrity Romantic Affairs Over the Years
Photo: John Lamparski/WireImage (Getty Images)

After being married for over two decades, Wendy Williams filed for divorce from her husband Kevin Hunter amid rumors that he had been cheating with a woman who gave birth to a baby in 2019. Wendy later revealed that Hunter was a “serial” cheater while they were married.

Advertisement

9 / 17

Cicely Tyson & Miles Davis

Cicely Tyson & Miles Davis

Image for article titled The Messiest Celebrity Romantic Affairs Over the Years
Photo: Robin Platzer/IMAGES (Getty Images)

The legendary entertainers were married from 1981 to 1988. Allegedly, Cicely Tyson lost her cool oftentimes and they were multiple rumors that Miles Davis cheated on her while they were together.

Advertisement

10 / 17

Marvin Gaye & Janis Hunter Gaye

Marvin Gaye & Janis Hunter Gaye

Image for article titled The Messiest Celebrity Romantic Affairs Over the Years
Photo: Michael Ochs Archives (Getty Images)

Marvin Gaye’s second wife, Janis Hunter Gaye, allegedly cheated on the legendary singer multiple times through the 1970s when they were married. In 2015, Jan released a book, After the Dance: My Life With Marvin Gaye, where she admitted to having an affair with R&B singers Frankie Beverly and Teddy Pendergrass. Janis died on Dec. 3 at the age of 66.

Advertisement

11 / 17

Dwayne Wade & Gabrielle Union

Dwayne Wade & Gabrielle Union

Image for article titled The Messiest Celebrity Romantic Affairs Over the Years
Photo: Edward Berthelot (Getty Images)

Dwayne Wade has been pretty open about his infidelity issues. He cheated on his childhood sweetheart, Siohvaughn Funches-Wade, with Gabrielle Union. Then, years later, he turned around and cheated on Union and had a baby with another woman.

Advertisement

12 / 17

Usher & Tameka

Usher & Tameka

Was Usher Unfaithful to His Ex-Wife? | Oprah’s Next Chapter | Oprah Winfrey Network

On an episode of Oprah’s Next Chapter, Usher admitted to being unfaithful during his marriage with his ex-wife, Tameka Foster.

Advertisement

13 / 17

Kobe Bryant & Vanessa Bryant

Kobe Bryant & Vanessa Bryant

Image for article titled The Messiest Celebrity Romantic Affairs Over the Years
Photo: Kirby Lee/WireImage (Getty Images)

When Kobe Bryant cheated on his wife, it almost landed him in prison. During an infamous press conference with Vanessa, he denied having raped the woman who accused him of the crime but did admit to having an adulterous relationship with her.

Advertisement

14 / 17

Alicia Keys & Swizz Beat

Alicia Keys & Swizz Beat

Dr. Shefali, Alicia Keys, Mashonda Tifrere and Swizz Beatz attend The Secret to Co-Parenting and Creating a balanced family at 92nd Street Y on October 3, 2018 in New York City.
Dr. Shefali, Alicia Keys, Mashonda Tifrere and Swizz Beatz attend The Secret to Co-Parenting and Creating a balanced family at 92nd Street Y on October 3, 2018 in New York City.
Photo: Jason Mendez (Getty Images)

Before Swizz Beatz had a loving relationship with Alicia Keys, he was married to Mashonda, a successful singer and songwriter in her own right. While the three are now friends, Mashonda accused Swizz of cheating on Alicia while they were married.

Advertisement

15 / 17

Carmelo Anthony & Lala Anthony

Carmelo Anthony & Lala Anthony

Image for article titled The Messiest Celebrity Romantic Affairs Over the Years
Photo: Shareif Ziyadat (Getty Images)

The star basketball player and successful entertainer dated since 2004. LaLa decided to split with the NBA All-Star in 2017 after he was accused of cheating and having a baby with another woman. In June 2021, LaLa filed for divorce.

Advertisement

16 / 17

Lionel Ritchie & Brenda Harvey

Lionel Ritchie & Brenda Harvey

Image for article titled The Messiest Celebrity Romantic Affairs Over the Years
Photo: Ron Wolfson/Michael Ochs Archive (Getty Images)

Allegedly, Ritchie was caught cheating on his first wife, Brenda Harvey, with Diane Alexander, who ended up being his second wife. Reportedly, Harvey beat the crap out of Ritchie and Alexander when she caught them sleeping together. The encounter was hilariously described in an episode of The Boondocks.

Advertisement

17 / 17