Skip to content

20 Emmys Red Carpet Photos You Won't Believe Are 20 Years Old

TV's biggest stars looked very different in 1999.

To say that television looked different 20 years ago would be something of an understatement: TiVo had just been introduced, streaming hadn't yet arrived, and Jennifer Aniston and Brad Pitt were not even married (let alone divorced).

In 1999, HBO was earning accolades for its just-launched series Sex and the City and The Sopranos, shows that are often credited with forever altering the TV landscape. And while those series—and all of the other shows honored at the 1999 Emmys—have ended, most of the actors who attended the ceremony are more famous than ever.

Sure, the fashion was different, but the stars were just as luminous. Want proof? Here are 20 photos from the 51st Annual Primetime Emmys in 1999 that will stoke your nostalgia.

Julia Roberts and Benjamin Bratt

julia roberts and benjamin bratt at the 1999 emmy awards

One of the greatest relics from the four-year relationship between Julia Roberts and Benjamin Bratt? Her much hyped guest starring role on Law & Order, which starred Bratt from 1995 until 1999. The performance earned Roberts an Emmy nomination in 1999, but she ultimately lost to Debra Monk on NYPD Blue. Roberts was nominated again in 2014, but she still doesn't have an Emmy to her name.

John Lithgow

john lithgow at the 1999 emmy awards

John Lithgow's quirky behavior was part of his charm on 3rd Rock From the Sun. And in 1999, the actor won his third Emmy for playing alien Dick Solomon on the NBC series. Lithgow's eclectic career has also helped him nab Emmys for playing a serial killer (on Dexter) and Winston Churchill (on The Crown).

Halle Berry

halle berry at the 1999 emmy awards

A bare midriff at the Emmys is a bold choice, so kudos to Halle Berry for totally rocking it. Berry would win her first (and so far only) Emmy the following year when she played the title character in the HBO movie Introducing Dorothy Dandridge.

Camryn Manheim

camryn manheim at the 1999 emmy awards

Although she didn't win her second Emmy in 1999—losing to her co-star from The PracticeHolland TaylorCamryn Manheim stunned in silver. And the ABC legal drama still won big. It was the most awarded series at the 51st Emmy Awards, taking home four statues.

Lara Flynn Boyle

lara flynn boyle at the 1999 emmy awards

So many cast members of The Practice went for sparkling attire in 1999—they must have known they were going to have a good night. Sadly, Emmy nominee Lara Flynn Boyle hasn't been seen on our TV screens since 2008. Fans were hoping she might reprise her role as Donna Hayward on Twin Peaks: The Return in 2017, but alas.

The cast of Ally McBeal

ally mcbeal cast at the 1999 emmy awards

It was a good year for David E. Kelley. The creator of Ally McBeal and The Practice earned top honors for both shows, which were awarded Outstanding Comedy Series and Outstanding Drama Series, respectively. No one else has achieved that feat since. Ally McBeal broke Frasier's five-year streak, and the cast—including nominees Calista Flockhart and Lucy Liu—was clearly thrilled.

Jennifer Aniston and Brad Pitt

jennifer aniston and brad pitt at the 1999 emmy awards

Jennifer Aniston and Brad Pitt were still only dating when they attended the Emmys together in 1999; they were married the following year, and stayed together until 2005, when they divorced.

Aniston's twisted locks were a departure from her signature "Rachel" 'do from Friends (which lost Outstanding Comedy Series to Ally McBeal that year). And Pitt's whole aesthetic here was very Tyler Durden, which makes sense—this was also the year of Fight Club.

Lisa Kudrow

lisa kudrow at the 1999 emmy awards

Lisa Kudrow stood out in this shimmering black dress, and she must have stood out to Emmy voters, too: She was the only Friends lead actor to be nominated for an award at the 51st Emmys. Over the course of the show's run, Kudrow actually netted six nominations for playing Phoebe Buffay, winning once in 1998.

Martin Short

martin short at the 1999 emmy awards

You'd be forgiven for not recognizing Martin Short, who wore a fat suit to the 1999 Emmys as his character Jiminy Glick. Short was channeling the incompetent celebrity interviewer he created on The Martin Short Show and who later got his own spinoff, Primetime Glick, in 2001.

Sarah Michelle Gellar

sarah michelle gellar at the 1999 emmy awards

If you want to get angry, think about the fact that Sarah Michelle Gellar never earned a single Emmy nomination for her iconic work on Buffy the Vampire Slayer. The actor, who turned heads in this bright blue dress in 1999, does have a Daytime Emmy, which she won in 1995 for playing Kendall Hart on All My Children.

Dennis Franz

dennis franz at the 1999 emmy awards

Before Grey's Anatomy broke the record in 2016, NYPD Blue was ABC's longest running primetime drama, and a big part of the show's enduring success was Dennis Franz's work as Detective Andy Sipowicz. In 1999, he earned his fourth Emmy win for the role, and he ended his run with a total of eight nominations.

Gloria Reuben

gloria reuben at the 1999 emmy awards

Grey's Anatomy also beat ER for the record of longest running medical drama in TV history, but the latter series still had an impressive 15 seasons on the air. Gloria Reuben, nailing this polka dot dress, starred in 102 episodes as Dr. Jeanie Boulet, earning Emmy nominations in 1997 and 1998.

Julianna Margulies

julianna marguiles at the 1999 emmy awards

The Emmys have always loved Julianna Margulies: In 1999, she earned her fifth nomination for playing Carol Hathaway on ER. She ended up with another nomination the following year—and, a decade later, four more (including two wins) for her work on The Good Wife.

Leelee Sobieski

leelee sobieski at the 1999 emmy awards

Remember Leelee Sobieski? The '90s teen queen made a name for herself in movies like Never Been Kissed and Deep Impact. And her performance as the titular saint in the miniseries Joan of Arc earned her major acclaim in 1999, including her one and only Emmy nomination. If you feel like you haven't seen Sobieski in a while, that's because she retired from acting in 2012.

Christina Applegate

christina applegate at the 1999 emmy awards

It would be another four years before Christina Applegate would get her first Emmy nomination (and win!) for playing Rachel's sister Amy on Friends. But Applegate has been TV royalty since Married… with Children, on which she played Kelly Bundy for a staggering 11 seasons. In 1999, she sparkled in red sequins at the Emmys with her former husband, Johnathon Schaech.

Kim Cattrall

kim catrall at the 1999 emmy awards

Actors are not the characters they play. Case in point: Kim Cattrall's classic, understated dress, which looks way more Charlotte than Samantha. While Sex and the City and Sarah Jessica Parker were both nominated for Emmys in 1999, it would be another year before Cattrall would earn a nod of her own.

Debra Messing

debra messing at the 1999 emmy awards

Who would have thought that Debra Messing would still be playing Grace Adler in 2019? Will & Grace only got one nomination at the 51st Emmys, but Messing eventually ended up earning five, finally winning in 2003.

Gillian Anderson

gillian anderson at the 1999 emmy awards

The 51st Primetime Emmy Awards were the last time Gillian Anderson was nominated for playing Dana Scully on The X-Files. She won once, in 1997, but awards pale in comparison to helping create one of the most important TV characters of all time. Anderson will be playing Margaret Thatcher on the next season of The Crown, so it seems likely there's another nomination in her future.

Helen Hunt

helen hunt at the 1999 emmy awards

Emmy voters know what they like, and they really like Helen Hunt. She was nominated for every season of Mad About You. This was her fourth consecutive win, and her last—but only because the series ended in 1999.

Keri Russell

keri russell at the 1999 emmy awards

How's this for disrespect? Keri Russell never got a single nod for her era-defining work on Felicity. Emmy voters made up for that in 2016, when she was nominated for playing Elizabeth Jennings on The Americans. Well, they almost made up for it. Despite being nominated three times, Russell never won. Want more vintage celebrity style moments? Check out these 30 Celebrity Red Carpet Photos You Won't Believe Are 20 Years Old.

To discover more amazing secrets about living your best life, click here to follow us on Instagram!

Filed Under