Drew Barrymore and Cameron Diaz, a long lasting celebrity friendship
Jade Small
Jade Small
February 12, 2024 ·  4 min read

17 Celebrity Friendships That Stood the Test of Time

The modern world is a vicious place. So much comparison and jealousy surround us all and it makes finding true friends very difficult. It could be argued that celebrities find it even harder to find such companions, thanks to the immense amount of competition they face every day. In some cases, there are celebrities who have found long-lasting friendships together. They have endured so much together and supported each other, and nothing seems to be able to break their connection. Here are 17 celebrity friendships that have stood the test of time.

1. Tobey Maguire and Leonardo DiCaprio’s

Leonardo and Toby first met in 1987 at an audition. they were only 12 years old at the time, but their friendship lasted. Among other similarities they shared between each other, they were both raised by their single mothers.

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A post shared by Tobey Maguire (@tobeymaguir)

2. Drew Barrymore and Cameron Diaz

Here are two of everyone’s favorite Charley’s Angels. Since meeting on set, Drew and Cameron have friends for 18 years. Wen referring to her celebrity friendship with Diaz, Drew Barrymore once said: “We‘ve experienced birth, life, death, marriage, divorce — highs and lows, work, boyfriends, friends, travel — there is nothing we haven’t done together.”

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A post shared by Drew Barrymore (@drewbarrymore)

3. Tina Fey and Amy Poehler

These two were introduced by a mutual friend. They had an instant connection that has grown into a strong friendship. Lasting for 26 years, they are bound the remain close pals who support each other.

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A post shared by Amy Poehler And Tina Fey (@amyandtina)

4. Will Smith and DJ Jazzy Jeff

In 1985, this dynamic duo met. Together they formed the Hip Hop group called, DJ Jazzy Jeff & The Fresh Prince. their friendship has been one of the few everlasting celebrity friendships known to the red carpet.

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A post shared by DJ Jazzy Jeff (@djjazzyjeff)

5. Nicole Kidman and Naomi Watts

Both Naomi Watts and Nicole Kidman originate from Australia. Having this in common helped their friendship grow, and last for all these years.

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A post shared by Naomi Watts (@naomiwatts)

6. Kate Winslet And Leonardo DiCaprio

Since the Titanic was filmed, Leonardo and Kate have remained close friends. That is 25 years go! They worked so well together that their friendship formed on strong foundations.

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A post shared by Kate Winslet & Leo DiCaprio (@allaboutkleo)

7. Debi Mazar and Madonna

These two first connected in the elevator of a nightclub. A great night turned into an even greater friendship.


8. Richard Pryor And Gene Wilder

These two comedic actors were laughing from the beginning of their friendship. While they have both sadly passed, we hope they are still laughing together now.

Richard Pryor And Gene Wilder
Image credit: Twitter / @richardpryor

9. Matt Damon and Ben Affleck

These two met in 1987 in Cambridge, Massachusetts. They later went on to work together in Hollywood, but nothing has come between their friendship.

10. Michael Jackson and Elizabeth Taylor: a celebrity friendship lasting even in death

Michael may not be alive anymore, but their friendship lives on!

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A post shared by ✨MCHL JKSN✨ (@irrelevantmjspam)

11. Queen Latifah and Jada Pinkett Smith

Latifah and Pinkett met as teenagers. This means they knew each other before they became rich and famous. Their friendship has lasted till now and is most likely to last for the rest of their lives.

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A post shared by Jada Pinkett Smith (@jadapinkettsmith)

12. Dean Martin, Sammy Davis Jr. and Frank Sinatra

This trio has shared an unbreakable bond. They made up the musical group called “The Rat Pack,” where they sang songs and made people laugh.

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A post shared by The Rat Pack – The Summit (@theratpack_)

13. Henry Fonda and Jimmy Stewart

A republican and a democrat – who would have thought?

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A post shared by Erin Matthiessen (@erinmatthiessen)

14. Jennifer Aniston And Courtney Cox

Courtney and Jennifer have been friends since they acted together on TV. The show, “Friends” seems to have created friends. Not to mention friendships that lasted 28 years!

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A post shared by Courteney Cox (@courteneycoxofficial)

15. Oprah Winfrey and Gayle King

Gayle and Oprah met when they were in their early 20s when living in Baltimore. After a freak snowstorm, Gayle was left without a place to stay. Oprah kindly let her stay with her. Their friendship grew stronger with each year.

Oprah Winfrey and Gayle King
Image credit: Twitter / @William53604792

16. Sarah Jessica Parker and Andy Cohen

This friendship has been blooming since the ’90s. They were even each other’s dates for the 2018 met gala.

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A post shared by Sarah Jessica Parker Daily (@sjp_daily)

Read: Sylvester Stallone Gives Heartfelt Tribute To His ‘Good Friend,’ The Late James Caan


  1. 20 Famous Friendships That Have Stood the Test of Time.Mom. Bryanne Salazar. May 3, 2021
  2. These Are The 10 Longest Lasting Celebrity Friendships In Hollywood.The Things. Antonia Georgiou. June 4, 2021