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36,980 Sean Penn Photos and High-Res Pictures

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Browse 36,980 sean penn photos and images available, or start a new search to explore more photos and images.

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Acting couple Madonna and Sean Penn leave rehearsals for their play 'Goose and Tom Tom' in August 1986 in New York City, New York.

Madonna And Penn

Sean Penn poses in the photo booth during AARP's Annual Movies For Grownups Awards at the Beverly Wilshire, A Four Seasons Hotel on February 08, 2025...

AARP's Annual Movies For Grownups Awards - Photo Booth

Leonardo DiCaprio and Sean Penn attend the 83rd Annual Golden Globe Awards at The Beverly Hilton on January 11, 2026 in Beverly Hills, California.

CBS's Coverage of the 83rd Annual Golden Globe Awards - Show and Backstage

American singer Madonna with her husband, actor Sean Penn, 1986.

Madonna And Sean

Actor Sean Penn walks down a street in Kyiv on March 16 amid the Russian invasion of Ukraine. Sean Penn, who scored an Oscar for best supporting...

UKRAINE-RUSSIA-CONFLICT-WAR-CULTURE

Sean Penn attends the Opening Ceremony during the 17th Film Festival Lumiere on October 11, 2025 in Lyon, France.

Opening Ceremony - 17th Film Festival Lumiere

Sean Penn and Madonna perform onstage circa 1986.

Sean Penn and Madonna

Actor Sean Penn walks down a street in Kyiv on March 16 amid the Russian invasion of Ukraine. Sean Penn, who scored an Oscar for best supporting...

TOPSHOT-UKRAINE-RUSSIA-CONFLICT-WAR-CULTURE

Actor Sean Penn walks down a street in Kyiv on March 16 amid the Russian invasion of Ukraine. Sean Penn, who scored an Oscar for best supporting...

UKRAINE-RUSSIA-CONFLICT-WAR-CULTURE

Musician Madonna and actor Sean Penn attend the 5th Annual Sean Penn & Friends HELP HAITI HOME Gala benefiting J/P Haitian Relief Organization at...

5th Annual Sean Penn & Friends HELP HAITI HOME Gala Benefiting J/P Haitian Relief Organization - Arrivals

Filmmaker and actor Sean Penn arrives to attend the opening ceremony of the 17th edition of the Lumiere Film Festival, in Lyon, central eastern...

TOPSHOT-FRANCE-ART-CULTURE-CINEMA-FESTIVAL

Acting couple Madonna and Sean Penn leave rehearsals for their play 'Goose and Tom Tom' in August 1986 in New York City, New York.

Madonna And Penn

Sean Penn attends the Hammond Cinema Vanguard Award ceremony during the 41st Santa Barbara International Film Festival at The Arlington Theatre on...

Hammond Cinema Vanguard Award - 41st Santa Barbara International Film Festival

Actor Sean Penn backstage at 76th Annual Academy Awards, February 29, 2004 in Hollywood section of Los Angeles, California.

Actor Sean Penn At Academy Awards

Sean Penn attends the Los Angeles Premiere of Paramount Pictures' "September 5" at Paramount Pictures Studios on November 14, 2024 in Hollywood,...

Los Angeles Premiere Of Paramount Pictures' "September 5"

Singer Madonna and Actor Sean Penn ringside at Tyson vs Holmes fight Convention Hall in Atlantic City, New Jersey January 22 1988.

Madonna and Sean Penn In Atlantic City

Musician Madonna and actor Sean Penn attend the 5th Annual Sean Penn & Friends HELP HAITI HOME Gala benefiting J/P Haitian Relief Organization at...

5th Annual Sean Penn & Friends HELP HAITI HOME Gala Benefiting J/P Haitian Relief Organization - Arrivals

Actor Sean Penn walks down a street in Kyiv on March 16 amid the Russian invasion of Ukraine. Sean Penn, who scored an Oscar for best supporting...

TOPSHOT-UKRAINE-RUSSIA-CONFLICT-WAR-CULTURE

Sean Penn attends the 'Conversation with' Session during Day Six Of the 21st Marrakech International Film Festival on December 04, 2024 in Marrakech,...

21st Marrakech International Film Festival - Day Six

Sean Penn and Madonna attend Madonna and Steven Klein secretprojectrevolution at the Gagosian Gallery on September 24, 2013 in New York City.

Madonna and Steven Klein secretprojectrevolution

Actor Sean Penn and Singer Madonna ringside at Tyson vs Holmes Convention Hall in Atlantic City, New Jersey January 22 1988.

Sean Penn And Madonna In Atlantic City

Sean Penn attends the "One Battle After Another" New York Screening at The Film Society of Lincoln Center, Walter Reade Theatre on September 21, 2025...

"One Battle After Another" New York Screening

Sean Penn attends the Opening Ceremony during the 17th Film Festival Lumiere on October 11, 2025 in Lyon, France.

Opening Ceremony - 17th Film Festival Lumiere

Sean Penn attends the "One Battle After Another" New York Screening at The Film Society of Lincoln Center, Walter Reade Theatre on September 21, 2025...

"One Battle After Another" New York Screening

Benicio del Toro, Sean Penn and Leonardo DiCaprio attend Moët & Chandon At The 83rd Annual Golden Globe Awards on January 11, 2026 in Los Angeles,...

Moët & Chandon At The 83rd Annual Golden Globe Awards

Filmmaker and actor Sean Penn takes part in a master class during the 17th edition of the Lumiere Film Festival in Lyon, central eastern France on...

FRANCE-ART-CULTURE-CINEMA-FESTIVAL

Sean Penn and Leila George attend CORE Gala: A Gala Dinner to Benefit CORE and 10 Years of Life-Saving Work Across Haiti & Around the World at...

CORE Gala: A Gala Dinner to Benefit CORE and 10 Years of Life-Saving Work Across Haiti & Around the World

Actor Sean Penn carries belongings of a shelter camp resident as they are prepared to be relocated to a new camp April 10, 2010 in Petionville,...

UN Begins Removing Haitians From Makeshift Camps Ahead Of Rainy Season

Sean Penn attends the "Into the Wild" By Sean Penn Invitation during the 17th Film Festival Lumiere on October 12, 2025 in Lyon, France.

"Into the Wild" By Sean Penn Invitation - 17th Film Festival Lumiere

Sean Penn attends the "Daddio" premiere during the 2023 Toronto International Film Festival at TIFF Bell Lightbox on September 10, 2023 in Toronto,...

2023 Toronto International Film Festival - "Daddio" Premiere

Madonna and Sean Penn arrives at the 5th Annual Sean Penn & Friends HELP HAITI HOME Gala Benefiting J/P Haitian Relief Organization at Montage Hotel...

5th Annual Sean Penn & Friends HELP HAITI HOME Gala Benefiting J/P Haitian Relief Organization - Arrivals

Honorees Sean Penn, Leonardo DiCaprio and Benicio del Toro attend the Hammond Cinema Vanguard Award ceremony during the 41st Santa Barbara...

Hammond Cinema Vanguard Award - 41st Santa Barbara International Film Festival

Sean Penn attends the London Premiere of "One Battle After Another" at Leicester Square on September 16, 2025 in London, England.

London Premiere Of "One Battle After Another"

Sean Penn attends the "One Battle After Another" Premiere at Odeon Luxe Leicester Square on September 16, 2025 in London, England.

"One Battle After Another" London Premiere - VIP Arrivals

Sean Penn acceptance speech for Best Actor Award during The 76th Annual Academy Awards - Show at The Kodak Theater in Hollywood, California, United...

The 76th Annual Academy Awards - Show

Actor Sean Penn and his girlfriend Robin Wright with their baby daughter Dylan at their residence in Malibu, California.

Sean Penn and Robin Wright

Photo shows Madonna and Sean Penn attending a function.

Madonna and Sean Penn, 1986

Acting couple Madonna and Sean Penn leave rehearsals for their play 'Goose and Tom Tom' in August 1986 in New York City, New York.

Madonna And Penn

Musician Madonna and host Sean Penn attend the 5th Annual Sean Penn & Friends HELP HAITI HOME Gala Benefiting J/P Haitian Relief Organization at...

5th Annual Sean Penn & Friends HELP HAITI HOME Gala Benefiting J/P Haitian Relief Organization

Sean Penn and Leila George arrive at the "Meet Me In Australia" event benefiting Australia Wildfire Relief Efforts at Los Angeles Zoo on March 08,...

The Greater Los Angeles Zoo Association Hosts "Meet Me In Australia" To Benefit Australia Wildfire Relief Efforts - Red Carpet

Sean Penn attends the "One Battle After Another" London Premiere at Odeon Luxe Leicester Square on September 16, 2025 in London, England.

"One Battle After Another" London Premiere - Arrivals

Sean Penn celebrates Apple Original Films' "Bono: Stories of Surrender" Cannes Film Festival World Premiere at Le Panorama Rooftop on May 16, 2025 in...

After Party For The Apple TV+ Premiere For The New Apple Original Films Documentary "Bono: Stories of Surrender"

Sean Penn attends the "conversation with" session during Day Six Of the 21st Marrakech International Film Festival on December 04, 2024 in Marrakech,...

21st Marrakech International Film Festival - Day Six

Actor/director Sean Penn and Valeria Nicov arrive to attend the second day of the 21st Marrakesh International Film Festival in Marrakesh on November...

MOROCCO-ENTERTAINMENT-FILM-FESTIVAL

Sean Penn attends the Los Angeles Premiere of Paramount Pictures' "September 5" at Paramount Pictures Studios on November 14, 2024 in Hollywood,...

Los Angeles Premiere Of Paramount Pictures' "September 5"

Actor Sean Penn and his girlfriend Robin Wright with their baby daughter Dylan at their residence in Malibu, California.

Sean Penn and Robin Wright

Portrait of American actor Sean Penn wearing a half-smile, early 1990s.

Portrait of Actor Sean Penn

Gary Oldman, Robin Wright and Sean Penn circa 1990 in New York City.

Gary Oldman, Robin Wright and Sean Penn

American singer Madonna with her husband, actor Sean Penn, circa 1985.

Madonna And Sean

Sean Penn and Madonna

Mike Tyson vs Michael Spinks Fight at Trump Plaza - June 27, 1988

Sean Penn attends the Hammond Cinema Vanguard Award ceremony during the 41st Santa Barbara International Film Festival at The Arlington Theatre on...

Hammond Cinema Vanguard Award - 41st Santa Barbara International Film Festival

Sean Penn speaks onstage during CORE Livestream Benefit Concert Celebrating 15 Years Of Global Impact at Ross House on December 09, 2025 in Los...

CORE Livestream Benefit Concert Celebrating 15 Years Of Global Impact

Valeria Nicov and Sean Penn attends the Opening Ceremony during the 17th Film Festival Lumiere on October 11, 2025 in Lyon, France.

Opening Ceremony - 17th Film Festival Lumiere

Sean Penn speaks onstage during a CAA Screening and Filmmaker Q&A of "September 5" in Los Angeles at Creative Artists Agency on December 08 in Los...

CAA Screening and Filmmaker Q&A of “September 5” in Los Angeles

Sean Penn and Valeria Nicov attend the Ceremony Tribute to Sean Penn during Day Two Of the 21st Marrakech International Film Festival on November 30,...

21st Marrakech International Film Festival - Day Two

Sean Penn and Valeria Nicov attend the Tribute to Sean Penn during Day Two Of the 21st Marrakech International Film Festival on November 30, 2024 in...

21st Marrakech International Film Festival - Day Two

Actor Sean Penn backstage at 76th Annual Academy Awards, February 29, 2004 in Hollywood section of Los Angeles, California.

Actor Sean Penn At Academy Awards

American actor Sean Penn, wearing a green jacket and a baseball cap, is restrained by a man as fights with a photographer Anthony Savignano outside...

Sean Penn Fights Anthony Savignano

Madonna and Sean Penn leave their limo circa 1986 in New York City, New York.

Madonna And Penn

Acting couple Madonna and Sean Penn leave rehearsals for their play 'Goose and Tom Tom' in August 1986 in New York City, New York.

Madonna And Penn

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