15 Celebrity Couples who Ruled the 2000s

Ben Affleck and Jennifer Lopez dated from 2002 to 2004 after meeting on the set of “Gigli,” captivating the world as “Bennifer.”

Affleck and Lopez were one of the couples of the 2000s. They co-starred in “Gigli,” one of the most notorious flops of all time, and “Jersey Girl,” they were constantly papped together and walking red carpets, and Affleck even starred in the “Jenny From the Block” music video.
They got engaged in November 2002, but the wedding was postponed and eventually canceled. Affleck and Lopez called it quits in January 2004.
But, after 17 years, these two crazy kids in love are making it work once again. They’re officially back together, and Bennifer is just as captivating now as they were two decades ago.

Beyoncé and Jay-Z were one of the biggest A-list couples in music during the 2000s, and they still are today.

Beyoncé and Jay-Z started dating after they collaborated on the 2002 song “’03 Bonnie and Clyde,” which appeared on the rapper’s album “The Blueprint 2: The Gift & The Curse,” though they had met the year prior at a Vanity Fair shoot. She even appeared as his girlfriend in the music video, fueling speculation about their relationship.
The following year, Jay-Z appeared on his girlfriend’s song “Crazy in Love,” which was one of the biggest songs of the 2000s. They quietly tied the knot in 2008.
The next decade was filled with ups and downs for Beyoncé and Jay-Z, including three kids, numerous collaborations, a cheating scandal, and a groundbreaking album about said cheating scandal (“Lemonade”).

Nick Lachey and Jessica Simpson kicked off the reality TV craze with their show “Newlyweds.”

The 98 Degrees singer began dating Simpson in the late ’90s, but they officially tied the knot in October 2002 after a brief engagement. The next year, “Newlyweds: Nick and Jessica” premiered on MTV, changing the course of “celebreality” TV forever. The show ran for three seasons, mesmerizing everyone around the world with talk of “chicken of the sea,” and other hilarious scenes.
The show’s finale aired in March 2005, and their relationship wasn’t long for this world. They filed for divorce in November 2005, and they officially split in June 2006.

2000s teens everywhere were obsessed with the relationship of Adam Brody and Rachel Bilson, both on- and off-screen.

When “The OC” premiered in August 2003, fans were immediately drawn to the relationship between nerdy Seth Cohen and it-girl (with a secret heart of gold) Summer Roberts, played by Brody and Bilson respectively.
Fans were sent into an additional frenzy when it became clear that, just like Seth and Summer, Bilson and Brody were dating. They were together for three years, from 2003 to 2006, breaking up just before the fourth and final season premiered in November 2006.

Katie Holmes and Tom Cruise are another prime example of the celebrity portmanteau phenomenon: They had the nickname “TomKat.”

Few couples captivated the paparazzi in the mid-2000s like “TomKat,” as Cruise was one of the biggest movie stars of all time, and Holmes was America’s sweetheart fresh off the success of “Dawson’s Creek.”
From the somewhat strange story that Holmes had a poster of Cruise in her bedroom while growing up to the iconic couch-jumping rant during an interview with Oprah Winfrey, “TomKat” headlines were everywhere.
They began dating in April 2005 and announced they were having a baby in October that year. Their daughter, Suri, was born in April 2006, and they tied the knot in a lavish Italian wedding in November.
However, their marriage didn’t last. Holmes filed for divorce in 2012.

Cameron Diaz and Justin Timberlake began dating after meeting at the 2003 Nickelodeon Kids’ Choice Awards.

In the early 2000s, few couples seemed like a more fun hang that Diaz and Timberlake. They dated for four years before breaking up in 2007 — shortly after she introduced him as musical guest on “Saturday Night Live,” and the same year they co-starred in “Shrek the Third.”
However, they appeared to stay good friends, as they played love interests in 2011’s “Bad Teacher.”

Jake Gyllenhaal and Kirsten Dunst were introduced by Gyllenhaal’s older sister, Maggie.


Dunst and Maggie co-starred in 2003 film “Mona Lisa Smile.” During filming, she introduced Dunst to her younger brother, and the two began dating in 2002, becoming an indie super-couple until their breakup in 2004.

You may have forgotten about Jessica Biel and Chris Evans dating for five years from 2001 to 2006, but we haven’t.

Evans and Biel dated before Evans became Captain America, and even before he was Johnny Storm in 2005’s “Fantastic Four.” In fact, when they began dating, Biel was more famous, thank to her role as Mary Camden in “7th Heaven” from 1996 to 2006.
They ended up co-starring in two movies, 2004’s “Cellular” and 2005’s “London” — coincidentally, Jason Statham appeared in both movies as well — before their eventual breakup in 2006.

Kanye West and Alexis Phifer began dating in 2002, got engaged, and then broke up in 2008, inspiring some of West’s best music.

West and Phifer began dating two years before “The College Dropout” shot West into the stratosphere in 2004. Following a brief breakup, the two patched things up in 2005 and were engaged by 2006, all while West’s star continued to rise.
After the untimely death of West’s mother, Donda, in 2007, friends said West was “going through a rough time” and the couple split. Much of West’s 2008 breakup album “808s & Heartbreak,” one of the best breakup albums of all time, was reportedly inspired by the split.

Ashlee Simpson and Ryan Cabrera were also huge with the MTV set in the early 2000s.

The beginning of Simpson and Cabrera’s relationship was documented on her MTV series, “The Ashlee Simpson Show.” During the show, she starred in the “On the Way Down” music video as Cabrera’s love interest, which eventually led to them dating in real life. He inspired many of the songs on her first album, including her hit “Pieces of Me.”
They were broken up by 2005, remaining friends.

Macaulay Culkin and Mila Kunis low-key dated for most of the 2000s.

Culkin began dating Kunis in 2002, when she was voicing Meg on “Family Guy” and smack in the middle of her six-year run on “That ’70s Show.” By contrast, Culkin had retired from acting after being one of the biggest child stars of all time.
The two dated for the rest of the decade, dodging marriage rumors, before calling it quits in 2011.

Kelis and Nas were one of hip-hop’s most A-list couples.

In a very early 2000s move, Nas and Kelis met at an MTV party in 2002, dated for a year, and got engaged in 2004, and eventually got married in 2005. During their relationship they collaborated on multiple songs like “In Public,” “Blindfold Me,” “Hey Nas,” “American Way,” and more.
Unfortunately, Kelis filed for divorce from Nas in April 2009, while she was seven months pregnant with their son. Over the last decade since the divorce, they’ve been involved in a custody battle, during which Kelis accused Nas of cheating and being verbally and physically abusive. Nas denied those allegations.

Brad Pitt and Jennifer Aniston kicked off the 2000s with a wedding in July.

Pitt and Aniston were known as Hollywood’s golden couple — literally, they were blonde and bronzed. After dating for two years, they tied the knot in July 2000. Their wedding was such a media circus that helicopters flew around the mansion they’d rented for the big day.
The next year, Pitt, one of the biggest movie stars at the time, made a guest appearance on “Friends,” his wife’s sitcom — the biggest sitcom on TV at the time. He played Will, a nemesis of Aniston’s character, Rachel.
However, nothing gold can stay, and the two called it quits in 2005 — famously that year, Pitt began dating his “Mr. and Mrs. Smith” co-star Angelina Jolie.

Arguably, Brad Pitt and Angelina Jolie, or “Brangelina,” were an even bigger deal when they started dating in 2005.

Just one month after his divorce was announced, Pitt was spotted stepping out with Jolie. The two got serious fast, and the tabloids were eager to pit — no pun intended — Jolie and Aniston against each other.
After famously not tying the knot for years, they got married in 2012, after six kids together. In fact, the first photos of their first biological child, Shiloh, sold for a cool $4.1 million. The first photos of their twins, born in 2008, were sold for $14 million — the most expensive celebrity photos of all time.
Jolie filed for divorce in 2016, and the two were engaged in a custody battle until very recently.

After co-starring in one of the most iconic romance films of all time, Ryan Gosling and Rachel McAdams fell in love off-screen, too.

Even though they didn’t get along at first on the set of 2004’s “The Notebook,” their chemistry was too strong to be ignored, and they eventually began dating. They iconically accepted the MTV Movie and TV Award for Best Kiss with an on-stage reenactment of their famous movie kiss.
They dated from 2005 to 2007, briefly got back together in 2008, and called it quits that year for good.

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