However you're ushering in the holiday season, there's one cultural touchstone you may be forgetting—and no, it's not a defrosting Mariah Carey. We're talking about Jingle Ball, a festive annual concert usually held in December that started in 1996 and routinely pulls in some of the biggest artists in the industry. We're talking Beyoncé, Celine Dion, J.Lo, John Mayer, Shania Twain, Missy Elliott, Hilary Duff, Mandy Moore, Jonas Brothers, Miley Cyrus...we can go on and on (and we do, below). While originally hosted by New York's Z100, several other radio stations have since taken a page out of their book—and we have a ton of photos to prove it.
Even if you're not a music fan (or have no idea what we're talking about—which, fair), there's another reason to tune in: the outfits. Looking through the archives of 1990s and early 2000s-era concerts has gifted us with some pretty incredible Y2K fashion gems (low-rise jeans aside, the festive attire is a treat). Plus, there are throwback moments we totally forgot ever happened—like Britney hanging with 98 Degrees and Leighton Meester taking the stage. With that, happy scrolling.
Britney Spears and 98 Degrees (1998)
It's Britney (and, in a surprising crossover event, every member of 98 Degrees), bitch.
Brandy and Nick Lachey (2008)
Jingle Ball: Bringing celebs together for press photos since 1996!
Ashley Tisdale, Katy Perry, and The Veronicas (2008)
Like we said...
Ryan Seacrest and Paris Hilton (2004)
Ryan Cabrera (2004)
The nostalgia we have for Ryan Cabrera's hair alone...
The Pussycat Dolls (2005)
Pussycat Dolls reunion when?
Mariah Carey (2001)
Who do we think we are if we don't feature the self-proclaimed Queen of Christmas?
Danity Kane (2006)
The group's self-titled debut album was released this year. It was a good year.
Ashanti and Ja Rule (2002)
Consider this our petition for a new Ashanti and Ja Rule song.
Lindsay Lohan (2004)
Lindsay Lohan at Jingle Ball the same year Mean Girls came out. (There's a "Jingle Bell Rock" pun in here somewhere.)
Joel and Benji Madden (2004)
Peace, love, and two-fifths of Good Charlotte (right around the time Joel was dating Hil).
Leighton Meester (2009)
Lest you forget: Leighton Meester had a music career at the same time she was starring on Gossip Girl.
Boyz II Men (1998)
A+ for the enthusiasm, A+ for the 'fits.
We dare you to find a more quintessentially 2000s outfit than this one (please note the low-rise jeans), courtesy of JoJo.
Jessica Simpson (2000)
There's festive, and then there's Jessica-Simpson-in-a-one-piece-Santa-outfit festive.
Jonas Brothers (2007)
Presented without comment: Some very 2000s-era haircuts on the Jonas Brothers.
A year after winning Billboard's Female New Artist of the Year, Pink (and her already-signature pink hair) appears at the 2001 Jingle Ball at Madison Square Garden.
Backstreet Boys (1997)
Pictured here in their peak '90s boy band glory are the Backstreet Boys, all following their own dress code.
Brandy and Lady Gaga (2008)
Brandy worked that '08 press room.
If you don't remember O-Town from MTV's "Making the Band," you're lying.
Mandy Moore (2000)
Mandy Moore, queen of Y2K fashion, in a befringed tank top with low-rise jeans before taking the stage.
Black Eyed Peas (2004)
Proof that the bucket hat trend defies time constraints: This pic of the Black Eyed Peas.
Lady Gaga (2008)
Here's Lady Gaga, dressed as a human crystal at her first-ever Jingle Ball, to help you consider a move to maximalism.
Jessica Simpson and Nick Lachey (2003)
This performance was probably featured on Newlyweds tbh.
Jesse McCartney (2004)
Is there anything that better encapsulates the early aughts than Jesse McCartney wearing a hoodie blazer on a red carpet?
Jennifer Lopez (1999)
Coinciding with the launch of her first album, J.Lo makes her inaugural Jingle Ball appearance in a line-up including Ricky Martin and Robbie Williams.
Hilary Duff (2004)
Everything okay, Hil?
Here's Queen B (the other members of Destiny's Child are just out of view) in a crop top set that wouldn't look out of place in 2023.
Taylor Swift (2009)
Taylor Swift, decked out as a disco ball, performs a few songs from her recently released Fearless album. Little did she know the superstardom that was ahead...
Ne-Yo and Brandy (2008)
Brandy found Ne-Yo backstage too!
A very, very early-stage Rihanna (her debut album had come out mere months prior) poses backstage at Madison Square Garden.
We love seeing celebs embracing the Santa hat!
Michelle Branch (2001)
TBT to us singing "Everywhere" at the top of our lungs in our rooms when our parents weren't home.
Hilary Duff (2003)
If this photo doesn't say 2003, IDK what does.
Ashlee Simpson (2004)
Her debut album, Autobiography, had just been released earlier that year, and let me tell you...ZERO SKIPS.
Britney Spears (2000)
Honestly, not mad at a single part of this outfit. Our GIRL.
Britney Spears (2000)
We're not done yet. Brit was having a blast!
Celine Dion (1997)
That's right: Celine Dion herself graced the Jingle Ball stage in 1997.
Missy Elliott (2001)
Fresh off the release of her third album, Missy Elliott gives an energetic performance in red leather and patchwork denim.
Jason Mraz (2003)
Jason Mraz: Festive and caffeinated.
Christina Aguilera (2000)
The gold lamé bralette! The low-rise belt! The romper with 'X-Tina' bedazzled on the arms! It's altogether a perfect ensemble for performing at Jingle Ball in 2000.
Janet Jackson (2009)
This is how Janet Jackson should always exist: on stage, surrounded by a cloud of multicolored confetti.
Hilary Duff (2003)
The next time you think about paring back your baubles, take some style cues from an early aughts Hilary Duff.
There aren't many people who could make a deconstructed button-up work, but then again, most people aren't Shakira.
Jon Bon Jovi (2000)
Honorable mention for this performance goes to the tomato-red bomber jacket.
Shania Twain (1998)
Leather, leopard, and a guitar—this is the Shania we know and love.
Mischa Barton (2003)
Let this pic of Mischa Barton attending Jingle Ball in '03 serve as a reminder to hydrate (and pull that off-the-shoulder sweater out of the closet).
Breanna Conrad (2006)
If you don't immediately recognize Lauren Conrad's younger sister, did you even watch Laguna Beach?
With a newly released album to promote, Ciara makes an appearance at Fort Lauderdale's version of Jingle Ball in 2006.
Coming off the release of their 12th (!!) album, Aerosmith takes to the stage.
Vanessa Hudgens (2006)
2006 was a banner year for Vanessa Hudgens: High School Musical came out, she performed at Jingle Ball, and she tracked down our dream sequin mini.
Gwen Stefani (2004)
Probably definitely singing "Hollaback Girl."
Timbaland and JoJo
BRB while we play "Lose Control (feat. JoJo)."
Fiona Apple (1997)
Our new life goal is to be as blissful as Fiona Apple on this Jingle Ball stage.
We're here for Jewel's bright red top that features not one, but two, types of straps—as well as a cut-out design.
Mariah Carey (2002)
🎵 Santa Baby 🎵
Alicia Keys (2001)
There to perform songs off her first-ever album, Alicia Keys makes a case for the denim-on-denim look.
Ashley Tisdale (2007)
Oh to be Ashley Tisdale's dog and serve as a plus-one to this 2007 Jingle Ball.
Will Smith (2005)
Just in case you forgot Will Smith is a triple threat, here's your reminder.
Kylie Minogue (2002)
Kylie Minogue may be the only person on Earth who can pull off Chanel earrings, sequined pants, and a truly confounding beaded top all at the same time.
Jack McBrayer (2008)
30 Rock fans, this one's for you.
Katy Perry (2008)
Listen, no one's ever accused Katy Perry of not committing to a theme.
Ricky Martin (1999)
'90s Ricky Martin is the best Ricky Martin.
Kelly Clarkson (2003)
This would've been the same year as her debut album release!
Michael Imperioli (2002)
Before he was in The White Lotus, he was providing excellent suiting inspo.
We're just now realizing that Bey performed at quite a few Jingle Balls—and now we're mad we didn't attend more of them back in the aughts.
Destiny's Child (2004)
With Destiny's Child at the time, of course!
John Mayer (2002)
John Mayer, in his most festive attire, takes to the stage to perform his setlist.
Justin Timberlake (2000)
A still-in-NSYNC Justin Timberlake looks pretty jazzed to be there in 2000.
Avril Lavigne and Kelly Osbourne (2002)
A post-Let Go Avril Lavigne strikes a pose with pal (and Ozzy and Sharon offspring) Kelly Osbourne.
Natasha Bedingfield (2005)
The British singer hopped the pond to perform at the 2005 Jingle Ball.
Lenny Kravitz and Jay-Z (2001)
A moment for Lenny Kravitz, king of winter accessories, and his layered hats.
The glitter, the eyeliner, the dollar sign... this is truly Ke$ha in peak form.
Jordin Sparks (2007)
Just off her American Idol win, Jordin Sparks (and her Hello Kitty-meets-NYC top) poses for photos backstage.
Miley Cyrus (2009)
This gallery would not be complete without Miley. Period.
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