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Old School Cool: Some of the greatest photos ever taken

By Carl Seaver

Last updated on June 24th, 2024 at 12:45 am

There’s cool, and then there’s the timeless “old-school cool.”

Whether it’s the punks of the 1980s or sophisticates from the 1880s, each period has its own version of cool.

Let’s take a moment to reminisce about the rad, the awesome, and the awe-inspiring figures from the past

A man and his beloved pet duck that he raised from an egg, 1994.

Susan Kare, famous Apple artist who designed many of the fonts, icons, and images for Apple, NeXT, Microsoft, and IBM. (1980s)

The Three Stooges visiting Yellowstone in 1969.

The Undertaker poses with an older woman, c. 1990s

Phil Collins in the 1990s.

Epic 80s moments

Uncle and Nephew playing poker, c. 1978.

Dolly Parton, 1970s

Burlington Mayor Bernie Sanders picks up trash on his own in a public park after being elected in 1981.

Carrie Fisher feeds Meryl Streep chocolate cake, 1991

Mark Hamill and Annie Potts on the set of Corvette Summer, 1978.

Heading to a concert in 1977.

A young Phil Collins in the 1960s.

Sarah Jessica Parker, Rob Lowe, and Robert Downey Jr. at the Governors Ball, 1988.

Prince stands victorious over Charlie Murphy during a game of basketball, 1985.

Heath Ledger’s Polaroid selfie with Larisa Oleynik, Joseph Gordon-Levitt and Julia Stiles on the set of 10 Things I Hate About You, 1999.

Hippie dad walking with his daughter. Amsterdam,1968

A 17-year-old’s yearbook photo, 1970s.

Kurt Cobain with his girlfriend Tracey, 1980’s

Awesome frog Halloween costume, 1977.

Larry Nance at the inaugural NBA Slam Dunk Contest – 1984

Johnny Depp and Salma Hayek at a party, Hollywood, 1995.

Vincent Price, Carrie Fisher, Ringo Starr and John Ritter, 1978.

Princess Grace of Monaco visiting JFK at the White House, 1961.

Ryan Dunn and Bam Margera in their High School yearbook, 1990s.

Jim Carrey and Cameron Diaz and their stunt doubles on the set of The Mask, 1994

Britney Spears and Melissa Joan Hart on the set of the (You Drive Me) Crazy music video, 1999.

Queen Elizabeth with her mother in the 1990s

Sigourney Weaver and Mel Gibson pose for a photo in 1982

Fisher Stevens and Michelle Pfeiffer, 1992.

Sharon Tate at the premiere of Rosemary’s Baby, 1968.

Jennifer Lopez at her a birthday party in New York, 1999

Jayne Mansfield and Mariska Hargitay, 1960s

Dennis and Randy Quaid, 1982

Sean Penn’s yearbook photo, 1975.

Arnold Schwarzenegger, Hugh Hefner, and Wilt Chamberlain at the Playboy Mansion, 1977.

Sting, the wrestler, reading a Far Side book, 1980s

Mister Rogers throws the opening pitch at a 1988 Pittsburg Pirates game

A hippie teenager in the 70s

Sophia Loren and Jayne Mansfield, 1957.

Senior Picture, 1990.

Rowan Atkinson and Christian Bale, 1984.

The Storyville Jazz Club in Copenhagen, Denmark, 1952

Chris Farley and his dad in the 1990s

Judy Garland with her baby Liza Minelli, c. 1945.

Brittany Murphy, 1998.

Woman at the beach in 1910.

Marlène Jobert, French actress and the mother of Eva Green, 1970s

The cast of Pulp Fiction, 1994.

Mrs. Fields, the founder of the Mrs. Fields cookie company, 1982.

Kate Capshaw, Harrison Ford and Ke Huy Quan during the filming of Indiana Jones and the Temple of Doom in 1984

Ric Flair meets a 12-year-old Dwayne Johnson c. 1984

Freddie Mercury and Michael Jackson, early 1980s,

Nirvana at a party just before they became famous.

Cameron Diaz cheerleading in high school, 1989.

Jodie Foster rides a skateboard in Paris, 1970s.

Model Jenny Claire and her mini, 1972.

Robert Plant backstage with The Runaways, 1975. Photo by Barry Schultz.

Bam Margera riding his first skateboard, 1988.

Tom Cruise and Rebecca De Mornay, 1983.

Dan Cortese, Jon Stewart. and George Clooney at MTV’s Rock & Jock Baseball, 1994.

Gary Oldman and Demi Moore, 1995

Original frontman of AC/DC Bon Scott in 1979

Jane Seymour, c.1970s

Linda Ronstadt, 1969

Debbie Reynolds with a Stanley cup, 1951

Bruce Springsteen, Michael Jackson and Billy Joel, 1985

Jerry Seinfeld and Larry David, 1989

Skateboarding in Uvalde, Texas, 1965.

Marlon Brando and photographer Mary Ellen Mark, 1970s

The ice man delivering a 25 pound block of ice, 1928.

First day in school for Mila Kunis, 1980’s.

Enjoying cocktails in the 1970s.

Barack Obama with a group of friends called the “Choom Gang” in 1979.

Nicolas Cage and his father, August Coppola, 1988

A same high party in 1997.

Christian Bale at his 18th birthday party, 1992

A wedding in 1949.

Chi Chi Rodriguez and his cool caddie John Lynch at the 1975 masters.

Lynda Carter representing Arizona at the Miss World USA 1972

My Mom on her wedding day in November, 1951

Albert Einstein at the Beach, 1939.

7 year-old George Clooney, 1968

Penelope Cruz and Salma Hayek, 1990s.

Princess Diana look-alike contest in Washington D.C., 1985

Stephen King opens the gates to his new Victorian-style house, guarded by bats. November 1982

Fifth Avenue, NYC, 1972.

Dolly Parton, 1960s.

Cybill Shepherd, 1972

Britney Spears in Tokyo, 1999

Helen Mirren, 1970s

Jayne Mansfield, 1960

Sally Fields, 1970s

Sandra Bullock, 1990s

Joaquin Phoenix and River Phoenix, with their parents and siblings, Summer,Liberty & Rain at home in LA California circa 1983

Sting giving his autograph to a young Gwen Stefani, 1983

Anthony Bourdain at his High School Graduation, New Jersey, 1974

Rose Byrne and Heath Ledger, 1999

Catherine O’Hara, 1970s

Anita Ekberg, 1950s

Betty White in 1948

The Beatles waiting to cross Abbey Road, 1969

Jimi Hendrix aged 15, with his first electric guitar

Michael and Shakira Caine, 1973

Winona Ryder, Jodie Foster and Julia Roberts in 1989

14-year-old Sigourney Weaver attends a Beatles concert at the Hollywood Bowl, 1964

Molly Ringwald, 1985.

Shakira, 1990.

Danny DeVito at Oratory Preparatory School, Summit, NJ, 1961

Drew Barrymore at 9 lighting Stephen King’s cigarette, 1984

Michael Jackson, 1980s

John Wayne on Vacation in Acapulco, 1959. Photo by Phil Stern

Willie Nelson in 1960

Keanu Reeves, 1990s

Arnold Schwarzenegger and Grace Jones on the set of ‘Conan the Destroyer,’ 1984

Ladies of the 70s

Actor Sean Connery reading while doing push-ups, 1957.

Jane Russell drawing Marilyn Monroe behind the scenes of Gentlemen Prefer Blondes, in 1953.

Pictures of Buddy Holly and his fans taken backstage, 1959.

The first selection of the Miss Slender Legs competition, Miami, 1952.

Photographer Ansel Adams, 1950

Marilyn Monroe with Lassie, 1950s.

Harry Belafonte and Dorothy Dandridge, 1950s

Marilyn Monroe and Arthur Miller on their wedding day, 1956

A woman is ticketed for wearing a bikini, 1957.

The employee cafeteria at Disneyland, 1961.

Peter Dinklage in high school.

Sean Connery, 23.

A woman cuts her birthday cake in Iran, 1973

Prince, 17.

Young FDR Jr. in 1937 at age 23.

A young woman photographed in the 1910s.

A cowboy, 1890s.

3 young women eat spaghetti on inflatable mattresses, 1939.

Two ladies ride in an early car model, 1900.

A cool girl posing with her car around 1920.

This mirror portrait was taken 100 years ago in Japan.

New car in South Richmond, Virginia, 1938.

Taking a break while building the Chrysler Building, New York, 1930.

A Victorian Girl from the 1860s!

A stylish family outing in 1946.

David Lee Roth and his signature leap circa 1982

Valerie Bertinelli and Eddie Van Halen getting married in 1981

Robert Downey jr at the academy awards 1993

Hedy Lamarr photographed by Alfred Eisentaedt, 1938

Jayne Mansfield, 1950s

Grace Kelly, 1950s

“How’s your leg?” Grace Kelly’s entrance scene in “Rear Window”-1954

Lauren Bacall and Marilyn Monroe at the premiere of “How to Marry a Millionaire,” 1953

Marilyn Monroe and Sammy Davis Jr. publicity photographs for “How to Marry a Millionaire,” 1953.

Lana Turner, Judy Garland, and Hedy Lamarr on the set of Ziegfeld Girl, 1941.

Marilyn Monroe photographed by Bruno Bernard at Racquet Club Resort Hotel in Palm Springs, 1949.

Elizabeth Taylor on the set of Giant, November 1956

Audrey Hepburn hanging out with Dean Martin and Jerry Lewis at Paramount Studios, 1953

Marilyn Monroe in cat-eye glasses, 1950s.

Barbara Stanwyck, 1920s

Lana Turner – “The Postman Always Rings Twice” 1946

Hedy Lamarr, 1940s

Lauren Bacall, Humphrey Bogart and Marilyn Monroe-1953 Oscars by Michael Ochs Archives

Judy Garland with her baby Liza Minelli, 1947

Lucille Ball, 1940s

Johnny Cash eating cake in a bush, 1971.

Clara Bow, 1927

A young Agatha Christie.

Gillian Anderson, 1990’s

David Bowie, 1975

Cameron Diaz and Jim Carrey at Cannes Festival, 1994

Fans watching the 1992 MLB All-Star Game in San Diego

English singer, songwriter Kate Bush, 1978

A Teenager At An Elvis Presley Concert At The Philadelphia Arena 1957

Joan Jett, 1977

Mike Tyson playing Punch Out, NES • 1987

Sid Vicious, Baton Rouge 1978

Jimi Hendrix and The Who at the Monterey Pop Festival, 1967

One of the first pictures taken of Black Sabbath, 1968.

Kurt photographed by his sister, Kim Cobain, Aberdeen, WA, September, 1986

Alice Cooper drinking a beer with Colonel Sanders

Sister Rosetta Tharpe: The Godmother of Rock & Roll.

Tina Weymouth – the bassist of Talking Heads, 80s.

Keith Richards in Seattle airport on the 1972 Stones tour of the USA

Ozzy Osbourne, 1976

David Gilmour, Pink Floyd. Live At Pompeii 1971.

Ozzy Osbourne, dressed as a ’50s housewife, ironing his daughter Aimee, 1984

Stevie Nicks working on Rumours, 1976

Bob Marley, Mick Jagger and Peter Tosh

Louis Armstrong plays for his wife, Lucille, in front of the Sphinx and Great pyramids in Giza, Egypt, 1961

Waylon Jennings and Johnny Cash

Les Paul and Paul McCartney

Muhammad Ali and The Beatles, 1964

Dolly Parton, live late ’60’s

Candice Bergen photographed by Milton Greene, 1966.

Dustin Hoffman and Jon Voight in Midnight Cowboy, 1969.

In 1956, Marilyn Monroe poses for photographers as she boards an American Airlines plane from New York.

Seventeen-year-old Elizabeth Taylor washing her golden cocker spaniel.

Vivien Leigh in a publicity photo for Waterloo Bridge, 1940.

Joséphine Baker, France, 1920

Vivian Leigh in ‘Caesar and Cleopatra,’ 1945.

Joanne Woodward and Paul Newman in Paris during the filming of Paris Blues, 1961.

Dean Martin, Kirk Douglas, Jimmy Durante, and Tony Curtis at a Friars Club event, in the late 1950s.

Publicity photo of Carole Lombard, 1935.

Joan Fontaine and Laurence Olivier in Rebecca, 1940.

Paul Newman in Cool Hand Luke, 1967.

Kim Novak and James Stewart in Vertigo, 1958.

Ingrid Bergman and her daughter Isabella Rossellini.

Elizabeth Taylor c. 1951.

Robert Redford and Barbra Streisand in ‘The Way We Were,’ 1973.

Audrey Hepburn in My Fair Lady, 1964.

Janet Leigh and Tony Curtis at home with their daughters, Jamie Lee and Kelly in 1959.

Jacqueline Kennedy and Princess Grace Kelly of Monaco, 1966.

Alma Reville with the prop head of her husband, Alfred Hitchcock, 1972.

Lauren Bacall, Humphrey Bogart, and Katharine Hepburn arriving in London after the filming of “The African Queen”

Gregory Peck and Brock Peters in To Kill a Mockingbird, 1962.

Jessica Tandy, 1949

Don Johnson and Melanie Griffith

Vivien Leigh behind the scenes of Gone with the Wind, 1939.

Grace Kelly, c. 1955.

Katharine Hepburn on the set of The Philadelphia Story in 1940.

Janet Leigh, 1950s.

Audrey Hepburn, Rex Harrison, and director George Cukor, My Fair Lady, 1964.

Marilyn Monroe, 1950s.

Susan Hayward “I Want to Live!” Best Actress Oscar, 1958.

Joanne Woodward and Paul Newman dancing at an after-party celebrating her Oscar win for “Three Faces of Eve,” 1958.

Jack Nicholson and Barbra Streisand during an Academy Awards party in 1970.

Elizabeth Taylor with her Oscar for Best Actress in “Butterfield 8” at the Academy Awards, 1961.

Elizabeth Taylor smiles while walking with her second husband, British actor Michael Wilding, at the Academy Awards in 1954.

Robert De Niro and Meryl Streep in Falling in Love, 1984

Teenage Elvis with his cousin Harold in 1953.

Steve McQueen at Paramount Studios Gym, 1962, by William Claxton.

Vivien Leigh pictured with her mother, Gertrude Hartley, circa 1922.

Doris Day at the Aquarium, jazz club on Seventh Avenue.

Sophia Loren Holding the chin of her sister, Maria.

Katharine Hepburn with her sisters Marion and Margaret, 1939.

After traveling for work, Josephine Baker greets three of her children at the airport in 1954.

Vivien Leigh, seen here at the Oscars ceremony in 1940 with Laurence Olivier.

Leonardo DiCaprio, Johnny Depp, and Brad Pitt.

John Wayne, with his son, on location in Mexico for the filming of “The War Wagon.”

The first meeting of Grace Kelly and Prince Rainier III of Monaco, 1955.

Marilyn Monroe surrounded by fan mail, 1955. Photo by Slim Aarons.

Dana Andrews & Teresa Wright in The Best Years of Our Lives – 1946.

Liberace and Elvis Presley jam backstage at a night club in 1956.

Elizabeth Taylor and daughter Liza Todd, c. 1950s.

Sophia Loren on the set of Yesterday, Today and Tomorrow, 1963.

Marilyn Monroe and Mickey Rooney at the premiere of ‘The Emperor Waltz’, 1948.

Christopher Lloyd (Banquo) and Christopher Walken (Macbeth) in the stage production Macbeth at Lincoln Center, New York, 1974

A young Slash with his parents, 1970

Shirley MacLaine with her brother, Warren Beatty in 1942.

1934 dance marathon participants at Crystal Lake Park in Marion, Ohio.

Princess Diana look-alike contest in Washington D.C., 1985

Liberace being seen off to France by a fan in the 1950s.

Elvis Presley and Cissy Houston (Whitney Houston’s mother), 1969

Michelle Phillips and Dennis Hopper’s during their 8-day marriage in 1970

Michael Caine at home with his mother, Ellen (1964)

Axl Rose sits handcuffed in the back of a police car after he was arrested at Kennedy Airport upon his return from a European concert tour, 1991. Photo by Bill Turnbull.

Frank Zappa with his parents, 1970

Jimi Hendrix getting his hair done. 1960’s

Joni Mitchell playing guitar for Eric Clapton and David Crosby, 1968

Linda Blair with Black Sabbath, 1976.

Lars Ulrich with his father, Tennis pro Torben Ulrich. Mid 1970s

Young men smoking, drinking, and playing cards Stetson University dorm room, Florida, ca 1900.

Janis Joplin pouring herself a drink before going on stage at Woodstock, 1969

Siouxsie Sioux, 1983

The Cure on Columbus Avenue, 1980

Lunch at the Universal studio commissary, 1963.

Andre the Giant holding up NFL quarterback Joe Theismann, 1975

Marilyn’s last photo taken by George Barris, 1962

A champagne inspector wearing a special mask to protect against accidental discharges, c. 1933.

24 Year-Old Orson Welles outside CBS’s Columbia Square studios at 6121 Sunset Boulevard on his first day in Hollywood, August 1939

A cop poses with some Flappers, Los Angeles, California, 1920s

Elton John at home with his collection of shoes, 1975.

Miss Idaho Potato, 1935

Alan Rickman, Hugh Laurie, Kate Winslet, Harriet Walter and Emma Thomson- 1994

Edward VIII wearing Japanese garb while on a tour of Japan as Prince of Whales in 1922

Crosby, Stills, Nash & Young, 1974. Photo by Joel Bernstein.

Mick Jagger and his bride Bianca at their wedding in 1971, Keith Richards in the background

‘The Half Suit’ Photo and concept by Pippa Garner, 1982

Zitkala Sa, Sioux Indian and activist, c. 1898.

The line to see Goonies on opening day at the Liberty Theatre in Astoria, Oregon way back in 1985.

The Who drummer Keith Moon playing pinball, sometime before September 1968

John Belushi, Muddy Waters, Johnny Winter, and Dan Aykroyd. 1977

Punk Rock girl London, 1979

A young Elizabeth/Liz Hurley at the Batcave in London, 1984.

William Shatner and Leonard Nimoy Taking a Lunch Break On the Star Trek Set

Change of swimsuit on the beach. 1930s

A woman and dogs spotted in Los Angeles, 1970.

The Clash & The Undertones photographed together in 1979

George Harrison photographed by Paul McCartney whilst on a hitchhiking trip to Wales in 1959.

John Lennon dancing with Louise Harrison, mother of George Harrison, at the Dorchester Hotel after the film premiere of, “A Hard Days Night” at the London Pavilion on July 1964.

Brian May, 1963

Diana Ross finishing up a Rib, 1980. Photographed by Ruven Afanador

The damned in New York, 1980’s

A vintage selfie from 1934

Burt Lancaster and Audrey Hepburn in The Unforgiven, 1960.

Karl Malden and Marlon Brando on the set of One-Eyed Jacks, 1961.

Cary Grant and Alfred Hitchcock on the set of North by Northwest, 1959.

Audrey Hepburn wears the costume for her Broadway debut in the play Gigi written by Colette and Anita Loos, photographed in 1952. Photo by Norman Parkinson.

Grace Kelly at the 8th Cannes Film Festival in 1955.

Jon Voight brings his children, Angelina Jolie and James Haven to the Oscars, 1988.

Robert Redford attends the premiere of All the President’s Men, in which he plays the legendary journalist Bob Woodward, in Washington, D.C. in 1976.

Audrey Hepburn in Roman Holiday (1953). Color by Klimbim.

Vivien Leigh and Lauren Bacall at a party celebrating the opening night of Duel of Angels on Broadway, 1960.

Sophia Loren in Scandal in Sorrento, 1955.

Clint Eastwood at home circa 1961.

Grace Kelly on the set of To Catch a Thief, 1955.

Janet Leigh, 1954.

Elizabeth Taylor with her Siamese cat (1956). Photo by Sanford Roth.

Tom Ewell and Marilyn Monroe in The Seven Year Itch, 1955.

Ingrid Bergman and her daughter Isabella Rossellini, 1960s.

Kirk Douglas, Jean Simmons, and Tony Curtis between scenes in Spartacus, 1960.

Frank Sinatra and his wife Nancy listening to music in their home in 1943.

Mel Ferrer and Audrey Hepburn in War and Peace, 1956

Audrey Hepburn greeting Barbra Streisand after watching her performance in Broadway’s Funny Girl at the Winter Garden Theatre in 1964.

Audrey Hepburn arrives at London Airport in 1953.

Robert Redford with journalist Bob Woodward on their way to the book party for All The President’s Men in June 1974.

Clint Eastwood, washing his car, North Hollywood, Calif., (1958) Photo by John R. Hamilton.

Joanne Woodward and Paul Newman, 1958.

Johnny Carson at 15 (1940).

Jane Fonda, younger brother Peter, father Henry Fonda, and his third wife Susan holding their daughter Amy.

Bette Davis, 1930.

Marilyn Monroe and Dale Robertson at a charity baseball game, 1952.

Paul Newman and Sophia Loren photo shoot for Lady L, 1965.

Dean Martin, Jerry Lewis, and Marilyn Monroe (1953).

Paul Newman and Elizabeth Taylor in Cat on a Hot Tin Roof, 1958.

Lucille Ball in 1935.

Tom Cruise, Matt Dillon, Patrick Swayze, Ralph Macchio, Emilio Estevez, C. Thomas Howell, and Rob Lowe on the set of “The Outsiders,” 1983.

Hattie McDaniel and Vivien Leigh in Gone with the Wind (1939).

Grace Kelly relaxing with family and friends aboard the Constitution. April, 1956.

Grace Kelly with her mother, Margaret, and sister, Lizanne, 1954.

Rita Hayworth standing on a yacht in a scene from Lady From Shanghai, 1947.

A young Elizabeth Taylor with a cat.

Elizabeth Taylor with her mother.

Joanne Woodward and Paul Newman relaxing at home.

Audrey Hepburn and Humphrey Bogart on the set of ‘Sabrina’ (1954).

Marilyn Monroe and Arthur Miller.

Sophia Loren and son Carlo Ponti Jr. at home, photographed by Alfred Eisenstaedt, 1969.

Olivia de Havilland by George Hurrell, 1938.

Bette Davis and her mother at the premiere of ‘All About Eve’ at Grauman’s Chinese Theater (1950).

Robert Redford and Meryl Streep in ‘Out of Africa’ (1985).

Laurence Olivier and Vivien Leigh.

Cary Grant and Marilyn Monroe on the set of Monkey Business (1952).

Elizabeth Taylor and Montgomery Clift in ‘A Place in the Sun’ (1951). 

Elizabeth Taylor and Richard Burton at the 1970 Academy Awards.

John Cassavetes and Gena Rowlands, August 1982.

Bette Davis on vacation in Hawaii after filming The Letter, 1940.

Rita Hayworth cooking at home, c. 1942.

Audrey Hepburn in Breakfast at Tiffany’s (1961).

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