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/ Source: TODAY
By Randee Dawn

In 1999, we were thinking about the new millennium, Y2K, Bill Gates turning into the wealthiest man in the world, a huge U.S. budget surplus, and President Bill Clinton's impeachment trial. Oh, yeah — and the 51st Primetime Emmy Awards, which in and of themselves were historic, too.

The pop culture world was changing, with original cable TV programming ascendant (thanks in large part to HBO's "The Sopranos"), Jon Stewart taking over Comedy Central's "The Daily Show," "All My Children" star Susan Lucci finally winning a Daytime Emmy after 18 previous nominations, and the premiere of "SpongeBob SquarePants."

But really, what about those Emmys, which were held on Sept. 12 at the Shrine Auditorium in Los Angeles? Well, a look back has to start with some of the big Hollywood pairings that strode down the red carpet, starting with ...

Brad Pitt and Jennifer Aniston.Dan Callister / Getty Images

Jennifer Aniston and Brad Pitt

Ah, memories. "Friends" star Aniston's show was nominated, and she had one of the hottest men in Hollywood on her arm: Brad Pitt and his interesting facial hair. They went on their first date in 1998 and were in the headlines constantly, so much so that 20 years later we still see stories in the news linking them. They wed in 2000, then separated in 2005. By the way, "Friends" lost that year to "Ally McBeal" in the outstanding comedy series category.

Julia Roberts and Benjamin Bratt.Jim Smeal / Ron Galella Collection via Getty Images

Julia Roberts and Benjamin Bratt

Long before settling down with current husband Danny Moder, America's Sweetheart Julia Roberts began dating "Law & Order" star Bratt. She earned her first Emmy nomination in 1999 for appearing on an episode of his show (in which their two characters had a serious flirtation), and the pair continued dating until 2001, a few months after he escorted her to the Oscars (where she won the Academy Award for best actress for "Erin Brockovich").

"Friends" stars David Schwimmer and Lisa Kudrow.Frank Micelotta / Getty Images

We're all 'Friends' here

"Friends" was in the middle of its super-hot run (the show would be on until 2004), and Lisa Kudrow had the sole acting nomination of the cast (she lost to "3rd Rock from the Sun" actress Kristen Johnson). The show would win the first of its two Emmys the following year — with a guest actor prize for Bruce Willis.

Eric Benet and Halle Berry.Frank Trapper / Corbis via Getty Images

High five

Halle Berry wasn't nominated for an Emmy in 1999, but her HBO film "Dorothy Dandridge" (which would earn her an Emmy in 2000) had just premiered, and in 2001 she'd become the first black actress to win best actress at the Oscars, for "Monster's Ball."

Sarah Michelle Gellar.Getty Images

Staking out the competition

With four movies coming out in 1999, including "Cruel Intentions," Gellar might not have been nominated for an Emmy, but the "Buffy the Vampire Slayer" actress was hugely popular and a welcome addition to the carpet. She has a Daytime Emmy award (for her work on "All My Children") but has never been nominated for a Primetime Emmy.

"Ally McBeal" cast Greg Germann, Lisa Nicole Carson, Portia De Rossi, Calista Flockhart, David E. Kelley (with his two Emmys), Lucy Liu, Courtney Thorne Smith, Vonda Shepard, and Jane Krakowski.Frank Micelotta / Getty Images

He's the man

David E. Kelley was one of the historic winners — twice over — on Emmy night. The creator and head writer for both "Ally McBeal" and "The Practice," Kelley set a new record as both series took home their respective outstanding series Emmy (comedy and drama). Plus, the star of "McBeal," Calista Flockhart (still a few years from connecting with Harrison Ford) looked radiant in a belly-baring knotted shirt and skirt.

Michelle Williams.Frank Micelotta / Getty Images

Up the 'Creek'

"Dawson's Creek" was a big hit among young audiences, but no one could have anticipated that Michelle Williams would end up as its breakout star. The show ended in 2003, and she would go on to marry actor Heath Ledger the following year. She earned the first of four Oscar nominations in 2006, for "Brokeback Mountain," and picked up her first Emmy nomination in 2019 for FX's "Fosse/Verdon," so we bet she'll be back this year.

Tracy Pollan, Michael J. Fox and son Sam.Frank Micelotta / Getty Images

Good 'Spin'

Eight years after his Parkinson's diagnosis, Fox was racking up some of the biggest honors of his career. He was nominated for "Spin City" four times, including in 1999, and would win his fourth of five (so far) Emmys in 2000 for the role. He showed up with wife Tracy Pollan and their son, Sam.

Cynthia Nixon, Sarah Jessica Parker, Kim Cattrall, and Kristin Davis of "'Sex in the City."Frank Micelotta / Getty Images

Plenty of 'Sex'

HBO's "Sex and the City" had premiered in 1998 and was taking the world by storm as everyone fell in love with Sarah Jessica Parker, Kim Cattrall, Kristin Davis and Cynthia Nixon. The four ladies shared the stage in support of Parker, who earned the show's first nomination, for outstanding lead actress in a comedy series. (She lost to Flockhart, above.) But the show would go on to earn 54 awards in total during its run, and took home the outstanding comedy series award in 2001. Parker was nominated every year from 2001 to 2004, and won the Emmy in 2004.

Jenna Elfman and a Q-tip. Er, David Hyde Pierce.Frank Micelotta / Getty Images

And now, presenting ...

"Hello, I'm Jenna Elfman," the star of "Dharma and Greg" announced at the start of the show, dressed in a purple exercise outfit; next to her stood "Frasier" star David Hyde Pierce in a matching purple unitard. "And I'm a Q-tip," he quipped dryly. The pair certainly kicked off hosting the show in a unique way, and we're not sure how much they got paid for their leotard dance interpretation, but there's no way it could have been enough.

Edie Falco.Frank Trapper / Corbis via Getty Images

A mother of an award

Edie Falco won for her role on "The Sopranos," a well-deserved honor indeed. But it wasn't just that this was her first-ever Emmy win; Falco became the first person from any cable TV series to win a major acting award. (HBO's "Dream On" had a guest Emmy winner in 1993, which went to David Clennon, hence the "major" emphasis here.) Falco would win the Emmy twice more for "Sopranos," in 2003 and 2004; she also won for "Nurse Jackie" in 2010.