22 Glorious Throwback Photos of Celebrity Friends You Never Knew Existed

Mar. 16, 2025

01of 22NICOLE RICHIE & RASHIDA JONESNicole Richie/InstagramThe Era:1980sWe Can’t Get Over …Richie’s A+ caption: “Dear @rashidajones please hold me now like you held me back then #tbt.”

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NICOLE RICHIE & RASHIDA JONES

Nicole Richie/Instagram

nicole-richie

The Era:1980s

We Can’t Get Over …Richie’s A+ caption: “Dear @rashidajones please hold me now like you held me back then #tbt.”

02of 22RACHEL ZOE & THE BACKSTREET BOYSRachel Zoe/InstagramThe Era:1999We Can’t Get Over …The stylist’s dark hair and the iconic boy band’s matchingMilleniumoutfits.

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RACHEL ZOE & THE BACKSTREET BOYS

Rachel Zoe/Instagram

rachel-zoe-backstreet-boys

The Era:1999

We Can’t Get Over …The stylist’s dark hair and the iconic boy band’s matchingMilleniumoutfits.

03of 22RASHIDA JONES & TRACEE ELLIS ROSSTracee Ellis Ross/InstagramThe Era:2000We Can’t Get Over …How these boss ladieshaven’t aged a bit.

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RASHIDA JONES & TRACEE ELLIS ROSS

Tracee Ellis Ross/Instagram

tracee-ellis-ross

The Era:2000

We Can’t Get Over …How these boss ladieshaven’t aged a bit.

04of 22JOSEPH GORDON-LEVITT & MICHELLE TRACHTENBERGJamie McCarthy/WireImageThe Era:2003We Can’t Get Over …The actors’totally 2003-era outfits. Hello, blazer-and-tee combo!

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JOSEPH GORDON-LEVITT & MICHELLE TRACHTENBERG

Jamie McCarthy/WireImage

2005 Sundance Film Festival - “Mysterious Skin” Cocktail Party

The Era:2003

We Can’t Get Over …The actors’totally 2003-era outfits. Hello, blazer-and-tee combo!

05of 22KIM KARDASHIAN WEST & NICOLE RICHIEKim Kardashian/InstagramThe Era:The ‘90sWe Can’t Get Over …How bare-faced and beautiful these two reality stars look. Also, we’re living for Nicole’s braces.

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KIM KARDASHIAN WEST & NICOLE RICHIE

Kim Kardashian/Instagram

nicole-richie

The Era:The ’90s

We Can’t Get Over …How bare-faced and beautiful these two reality stars look. Also, we’re living for Nicole’s braces.

06of 22EMINEM & JUSTIN BIEBERSource: Justin Bieber/InstagramThe Era:The 2010sWe Can’t Get Over …The fact that we almost forgot Eminem’s hair was black at one point andJustin’s hair was this flip-worthy.

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EMINEM & JUSTIN BIEBER

Source: Justin Bieber/Instagram

justin-bieber

The Era:The 2010s

We Can’t Get Over …The fact that we almost forgot Eminem’s hair was black at one point andJustin’s hair was this flip-worthy.

07of 22WILL SMITH, SALMA HAYEK & GEORGE CLOONEYSource: Salma Hayek/InstagramThe Era:The late ‘90sWe Can’t Get Over …The trio’s decision to all wear white shirts. Will, Salma and George clearly invented #squadgoalsyearsbefore it became a thing.

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WILL SMITH, SALMA HAYEK & GEORGE CLOONEY

Source: Salma Hayek/Instagram

george-clooney

The Era:The late ’90s

We Can’t Get Over …The trio’s decision to all wear white shirts. Will, Salma and George clearly invented #squadgoalsyearsbefore it became a thing.

08of 22HEIDI KLUM & TYRA BANKSJeff Vespa Archive/WireImageThe Era:2001We Can’t Get Over …How muchbeauty can fit into just one picture. Seriously, can we take a moment to acknowledge how ageless these supermodels really are?

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HEIDI KLUM & TYRA BANKS

Jeff Vespa Archive/WireImage

heidi-klum-tyra-banks

The Era:2001

We Can’t Get Over …How muchbeauty can fit into just one picture. Seriously, can we take a moment to acknowledge how ageless these supermodels really are?

09of 22ELIZABETH BANKS & JUSTIN THEROUXSource: Justin Theroux/InstagramThe Era:2005We Can’t Get Over …Justin’s braces, which he donned to play a lovestruck teenager alongside his feather-hairedThe Baxtercostar.

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ELIZABETH BANKS & JUSTIN THEROUX

Source: Justin Theroux/Instagram

justin-theroux-news

The Era:2005

We Can’t Get Over …Justin’s braces, which he donned to play a lovestruck teenager alongside his feather-hairedThe Baxtercostar.

10of 22MARIAH CAREY & WILL SMITHSource: Mariah Carey InstagramThe Era:No idea, but it’s totally timelessWe Can’t Get Over …Absolutely everything about this iconic moment. Mariah’s caption says it best: “I still can’t believe this picture …”

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MARIAH CAREY & WILL SMITH

Source: Mariah Carey Instagram

mariah-carey-2000

The Era:No idea, but it’s totally timeless

We Can’t Get Over …Absolutely everything about this iconic moment. Mariah’s caption says it best: “I still can’t believe this picture …”

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RYAN SEACREST, RANDY JACKSON & SIMON COWELL

RyanSeacrest/Instagram

ryan-seacrest

The Era:The early 2000s

12of 22JUSTIN TIMBERLAKE & MANDY MOORESource: Mandy Moore/InstagramThe Era:Summer of ‘99We Can’t Get Over …The Abercrombie shirts and bucket hats. (But neither can Mandy, TBH.) She would later recall her excitement over opening for ‘NSYNC … only for Justin to say, “You have big feet for a girl.” Well, the past is in the past.

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JUSTIN TIMBERLAKE & MANDY MOORE

Source: Mandy Moore/Instagram

mandy-moore

The Era:Summer of ‘99

We Can’t Get Over …The Abercrombie shirts and bucket hats. (But neither can Mandy, TBH.) She would later recall her excitement over opening for ‘NSYNC … only for Justin to say, “You have big feet for a girl.” Well, the past is in the past.

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THE CAST OFFREAKS & GEEKS

Source: Busy Philipps Instagram

busy-philipps-2000

14of 22JESSICA SIMPSON & SARAH MICHELLE GELLARSarah Michelle Gellar/InstagramThe Era:2000We Can’t Get Over …How their minimalist, spaghetti-strap dresses would look right at home inKendall JennerorGigi Hadid’s closets. Really, the only reason we know this pic wasn’t taken, like, yesterday is because of the lack of red-eye reduction (which Gellar totally laughed about on Instagram.)

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JESSICA SIMPSON & SARAH MICHELLE GELLAR

Sarah Michelle Gellar/Instagram

sarah-gellar

We Can’t Get Over …How their minimalist, spaghetti-strap dresses would look right at home inKendall JennerorGigi Hadid’s closets. Really, the only reason we know this pic wasn’t taken, like, yesterday is because of the lack of red-eye reduction (which Gellar totally laughed about on Instagram.)

15of 22MICHELLE TRACHTENBERG & GREGORY SMITHSource: Michelle Trachtenberg InstagramThe Era:1995We Can’t Get Over …Michelle’s epic ’90s style. The pint-sized star reminisced about the time she and her equally adorable costar worked on 1996’sHarriet the Spy— which started filming on her 10th birthday.

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MICHELLE TRACHTENBERG & GREGORY SMITH

Source: Michelle Trachtenberg Instagram

michelle-trachtenberg-2000

The Era:1995

We Can’t Get Over …Michelle’s epic ’90s style. The pint-sized star reminisced about the time she and her equally adorable costar worked on 1996’sHarriet the Spy— which started filming on her 10th birthday.

16of 22DESTINY’S CHILD & CO.Source: Beyonce InstagramThe Era:The early ’00s, most likelyWe Can’t Get Over …The serious girl powerBeyoncé, Kelly Rowland and Michelle Williams are serving up in this picture gives our lives so much meaning — as well as Ms. Tina and La La Anthony’s cameos.

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DESTINY’S CHILD & CO.

Source: Beyonce Instagram

beyonce-2000

The Era:The early ’00s, most likely

We Can’t Get Over …The serious girl powerBeyoncé, Kelly Rowland and Michelle Williams are serving up in this picture gives our lives so much meaning — as well as Ms. Tina and La La Anthony’s cameos.

17of 22BRITNEY SPEARS & LEONARDO DICAPRIOSource: Britney Spears InstagramThe Era:We’re guessing the early ‘00sWe Can’t Get Over …The fact that it took until 2016, whenBritney posted this snap to her Instagram, before we ever knew this moment happened. Oh, and Leo’s hand gesture, which we will spend the rest of our lives trying to understand.

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BRITNEY SPEARS & LEONARDO DICAPRIO

Source: Britney Spears Instagram

britney-spears-2000

The Era:We’re guessing the early ’00s

We Can’t Get Over …The fact that it took until 2016, whenBritney posted this snap to her Instagram, before we ever knew this moment happened. Oh, and Leo’s hand gesture, which we will spend the rest of our lives trying to understand.

18of 22SHARON STONE & DREW BARRYMORESource: Drew Barrymore InstagramThe Era:The ‘90sWe Can’t Get Over …And will never be over Drew’s infectious smile andSharon’s ability to stay ageless, no matter the decade.

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SHARON STONE & DREW BARRYMORE

Source: Drew Barrymore Instagram

drew-barrymore-2000

We Can’t Get Over …And will never be over Drew’s infectious smile andSharon’s ability to stay ageless, no matter the decade.

19of 22MICHELLE WILLIAMS & BUSY PHILIPPSSource: Busy Philipps Instagram; Astrid Stawiarz/Getty Images for Louis VuittonThe Era:2001We Can’t Get Over …This pair’s super tight bond, which began in theirDawson’s Creekdays and remains strong to this day. Also, Busy’s totally ’00s fashion sense, which she equates toherCougartowncharacter’s style.

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MICHELLE WILLIAMS & BUSY PHILIPPS

Source: Busy Philipps Instagram; Astrid Stawiarz/Getty Images for Louis Vuitton

busy-philipps-2-2000

We Can’t Get Over …This pair’s super tight bond, which began in theirDawson’s Creekdays and remains strong to this day. Also, Busy’s totally ’00s fashion sense, which she equates toherCougartowncharacter’s style.

20of 22BRITNEY SPEARS & ‘NSYNCSource: Chris Kirkpatrick TwitterThe Era:Around 2000We Can’t Get Over …How much prep it tookfor Britney and the ’90s boy band to looksogood, which ‘NSYNC member Chris Kirkpatrick is quick to poke fun at in his caption: “Hair you doin?”

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BRITNEY SPEARS & ‘NSYNC

Source: Chris Kirkpatrick Twitter

britney-n-sync-2000

The Era:Around 2000

We Can’t Get Over …How much prep it tookfor Britney and the ’90s boy band to looksogood, which ‘NSYNC member Chris Kirkpatrick is quick to poke fun at in his caption: “Hair you doin?”

21of 22HILARY DUFF, ADAM LAMBERG & LALAINESource: Lalaine Vergara/InstagramThe Era:The early 2000sWe Can’t Get Over …How much we misswatching this trio onLizzie McGuire. #NeverForget

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HILARY DUFF, ADAM LAMBERG & LALAINE

Source: Lalaine Vergara/Instagram

hillary-duff

We Can’t Get Over …How much we misswatching this trio onLizzie McGuire. #NeverForget

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DRAKE & MIRIAM MCDONALD

Source: Miriam McDonald/Instagram

drake

source: people.com