Brad Pitt’s Hair Through the Years:
#1 1980s: The Early Days

Brad Pitt attends the Seventh Annual Jimmy Stewart Relay Marathon Kick-Off Cocktail Reception on January 14, 1988 – @Getty
His acting career began in 1987.
#2 1991: “Thelma & Louise”

Juliette Lewis & Brad Pitt at the premiere of Thelma & Louise in Los Angeles on May 10, 1991 in Los Angeles – @Getty
In 1991, he played a supporting role in Ridley Scott’s film Thelma & Louise.
#3 1994: Long and Wild – “Legends of the Fall” Era

Brad Pitt and Jitka Poheldek at the Mann Village Theatre in Westwood at “Legends of the Fall” Los Angeles Premiere – @Getty
In 1994, Pitt starred in Legends of the Fall alongside Anthony Hopkins. The film was nominated for three Academy Awards.
#4 1995: The Tousled Grunge Look of “Se7en”

Brad Pitt attends the Seven New York City Premiere on September 15, 1996 at Alice Tully Hall, Lincoln Center in New York City – @Getty
In 1995, he played homicide detective David Mills in the crime thriller Seven. It also stars Morgan Freeman and Gwyneth Paltrow.
#5 1997: “The Devil’s Own” Hair Phase

Brad Pitt and Gwyneth Paltrow at “The Devil’s Own” Premiere – @Getty
In the 1997 film The Devil’s Own, Brad performed opposite Harrison Ford.
He dated Gwyneth Paltrow from 1994 to 1997.
#6 1999: Messy Perfection in “Fight Club”

56th Venice Film Festival: Photocall of “Fight club” – 1999 – @Getty
In 1999, he portrayed Tyler Durden in Fight Club. The New York Times dubbed it the “defining cult movie of our time.”
#7 2000: Brown hair in Snatch

‘Snatch’ Movie Stills -@Getty
In 2000, Pitt played as an Irish Traveller boxer in Guy Ritchie’s 2000 gangster film Snatch.
#8 2001: “Ocean’s Eleven” and the Return to Suave Short Hair

March 08, 2001 – @Getty
In 2001, he portrayed Rusty Ryan in the heist film Ocean’s Eleven, alongside his friends George Clooney and Matt Damon.
#9 2002: In love with Jennifer Aniston

Jennifer Aniston and Brad Pitt arriving at the Shrine Auditorium in Los Angeles for the 54th Annual Primetime EMMY Awards 09/22/02 – @Getty
From 2000 to 2005, he was married to Jennifer Aniston.
#10 2004: Long, Flowing Warrior Locks in “Troy”

On the Set of the Movie “Troy” – @Getty
In 2004, he started in Troy as Achilles. Troy made over $497 million worldwide.
#11 2005: The “Mr. & Mrs. Smith” Cut

@Getty
In 2005, Pitt played in the action comedy Mr. & Mrs. Smith. The film was a box-office success, grossing $487.3 million worldwide.
#12 2006: Gray hair in Babel

Brad Pitt on location in Morocco for the filming of ‘Babel’ – @Getty
In 2006, Pitt and Cate Blanchett performed in Alejandro González Iñárritu’s drama Babel.
#13 2008: Fresh style with Angelina Jolie

Brad Pitt and Angelina Jolie arrive for the premiere of ”Changeling” at the Ziegfeld Theater on October 4, 2008 in New York City – @Getty
Pitt and Angelina Jolie started dating in 2005 and later separated in 2016. They first met while filming Mr. & Mrs. Smith in 2003. Their divorce was finalized at the close of 2024.
#14 2011: “Moneyball” and the Long Hair Look

Brad Pitt speaks onstage at Moneyball Press Conference during 2011 Toronto International Film Festival – @Getty
In 2011, he starred in the sports drama film Moneyball. It was directed by Bennett Miller.
#15 2011: Slick hair at Cannes

Brad Pitt poses during the 64th Annual Cannes Film Festival on May 20, 2011 in Cannes – @Getty
Pitt participated at the 64th Annual Cannes Film Festival.
#16 2012: Again Slicked-Back Sophistication in “Killing Them Softly”

Brad Pitt is seen on the movie set of the ‘Killing Them Softly’ on March 11, 2011 in Now Orleans – @Getty
In 20012, Brad was seen in Andrew Dominik’s Killing Them Softly. The film grossed over $37 million against a budget of $15 million.
#17 2013: “World War Z” Brad Goes Rugged with Long Hair

Brad Pitt attends the World War Z New York Premiere at Duffy Square in Times Square on June 17, 2013 – @Getty
In 2013, Pitt starred as retired United Nations investigator Gerald “Gerry” Lane in the action horror film World War Z. It was a commercial success, grossing more than $540 million.
#18 2015: A New-Cut At The Sundance Film Festival

Brad Pitt attends the True Story premiere during the 2015 Sundance Film Festival – @Getty
At the 2015 Sundance Film Festival premiere of “True Story,” Brad Pitt showcased a hairstyle that blended classic elegance with a modern touch.
#19 2019: A “Once Upon a Time in Hollywood” Style

Brad Pitt attends the screening of Once Upon A Time In Hollywood during the 72nd annual Cannes Film Festival – @Getty
In 2019, the American actor starred in Once Upon a Time in Hollywood as Cliff Booth alongside Leonardo DiCaprio as Rick Dalton. In February 2020, he won an Oscar for best supporting actor for his performance in Once Upon a Time in Hollywood.
#20 2024: A serious cut in Wolfs

George Clooney and Brad Pitt attend the Venice International Film Festival photo call for “Wolfs” – @Getty
In 2024, Brad Pitt and his best friend George Clooney played in Wolfs. In the film, they are “professional fixers.”