Brad Pitt & Jennifer Aniston
Do these two even need an introduction? They were one of Hollywood's most beloved couples. And while things didn't work out romantically, we can't help but remember fond memories like this appearance at the 1999 Emmys.
Brad Pitt & Jennifer Aniston
They're back! At the 2000 Emmy Awards, fashion lovers loved the Friends star's sexy red dress and clutch. As for Brad's pose, there's just one word: Swag!
Brad Pitt & Jennifer Aniston
What's so funny you two? Little did pop culture fans know that the 2004 Emmys would be this pair's final appearance at the show as a couple. Don't cry because it's over; smile that it happened!
Justin Hartley & Chrishell Stause
Long before Selling Sunset revealed so much about this Hollywood split, the This Is Us star and Oppenheim Group real estate agent were a happy couple at the 2019 Emmys.
Ian Somerhalder & Nina Dobrev
Let's be honest: These two looked red hot at the 2011 Emmys when walking the red carpet. But we can't forget that both have moved on. In fact, Ian has started a beautiful family with Nikki Reed. Long live The Vampire Diaries.
Heidi Klum & Seal
Before marrying Tom Kaulitz, the Project Runway host was celebrating her achievements on the small screen with the "Kiss From a Rose" singer.
Eva Longoria & JC Chasez
At the 2004 Emmys, Desperate Housewives was just kicking off and creating buzz. One of the stars just so happened to have a boy band member as her plus one.
Will Arnett & Amy Poehler
Before announcing their separation in September 2012, this couple brought the laughs to every red carpet. And yes, Will was more than happy to support his wife's beloved comedy series Parks and Recreation.
Zooey Deschanel & Jacob Pechenik
Back in 2014, the actress celebrated the success of New Girl on the red carpet with her husband. Today, the couple is separating with Zooey dating Property Brothers star Jonathan Scott.
Jennifer Garner & Scott Foley
Rewind to the 2002 Emmys when the Alias stars were happily married after meeting on set. The two would later separate in March 2003 with their divorce being finalized almost one year later.
Jame-Lynn Sigler & Jerry Ferrara
After meeting on the set of Entourage in 2008, these two developed a romantic relationship that included a date night at the 2009 Emmy Awards. The couple would later split in December of the same year.

