400 Reasons Why Old School Cool Images Remain Timeless

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.

Princess Diana visiting the Pyramids.

Sigourney Weaver and Winona Ryder, 1997

Johnny Cash on the set of Sesame Street, 1973

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

Joi Lansing (1956).

Raquel Welch, FLAREUP, 1969

Lynda Carter being carried by her stunt double Jeannie Epper, 1975.

A group of girls in New York City’s subway, circa 1970

Carrie Fisher listening to Mark Hamill’s first son, 1979

Susan Kare, famous Apple artist who designed many of the fonts, icons, and images for Apple, NeXT, Microsoft, and IBM. (1980s)
Lynda Carter, 1970s

Lynda Carter in the 80s

Phoebe Cates in TV movie “Baby Sister.” [1983]

Raquel Welch, 1966

The Three Stooges visiting Yellowstone in 1969.
Monica Bellucci, 1991

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

Phil Collins in the 1990s.

Epic 80s moment

Steven Spielberg relaxing between takes while shooting Jaws. 1975.

Uncle and Nephew playing poker, c. 1978.

John Wayne with his 3-year-old grandson on the set of The Big Jake

Pedro Pascal with his family in 1991.

Groucho Marx suffered from severe insomnia. When he couldn’t sleep, he would call his neighbour, Alice Cooper, and ask him to come over and join him. Alice would bring over a six-pack of beer and Groucho and he would drink beer and watch old movies on TV until Groucho nodded off. (1974)

Dolly Parton, 1970s

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Opera diva Maria Callas meets Marilyn Monroe during the Birthday party of JFK in Madison Suqare Garden, NY, 19 of May of 1962. 

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

Carrie Fisher (1983)

Isabella Rossellini and Monica Bellucci, 1995

Steve Irwin, aged 17, playing for the local rugby league team. 1979. 

Carrie Fisher feeds Meryl Streep chocolate cake, 1991

Elton John Dodger Stadium Oct. 26, 1975

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

Heading to a concert in 1977.

Monica Bellucci, 1990

Bruce Springsteen in 1970 at 20

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.

(1978) Carrie Fisher in a trash can

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

Monica Bellucci in movie La Riffa (1991)
Fisher Stevens and Michelle Pfeiffer, 1992.
Jennifer Lopez at her a birthday party in New York, 1999

Jayne Mansfield and Mariska Hargitay, 1960s

Dennis and Randy Quaid, 1982
The 16 Year Old that Sailed Around the World with his Cat, 1965

Sting, the wrestler, reading a Far Side book, 1980s
A hippie teenager in the 70s

Ozzy Osbourne and his wife Sharon in 1984.
Senior Picture, 1990.

Rowan Atkinson and Christian Bale, 1984.
Michelle Pfeiffer as Catwoman, on the set of Batman Returns, 1992

Lisa Kudrow & Jennifer Aniston, 1995
“My great grandfather, when he was Chief of my reservation in the 70s” – u/r fanman5000 on Reddit

Brittany Murphy, 1998.
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
Seth MacFarlane in 1999

Filming that iconic pool scene, Fast Times at Ridgemont High, 1982

Brad Pitt and Jennifer Aniston at a Radiohead concert, 1998

Christina Ricci and Jimmy Workman behind the scenes of The Addams Family, 1991.
Freddie Mercury and Michael Jackson, early 1980s,
Phoebe Cates, 1980s
Robert Plant backstage with The Runaways, 1975. Photo by Barry Schultz.

Robert Plant of Led Zeppelin holding a dove that flew into his hand during a concert in 1973.

Bam Margera riding his first skateboard, 1988.
Nicolas Cage took his son, Weston, backstage at a WWF event to meet the Chyna 1998
Bryan Cranston and his wife, 1989
Phoebe Cates – Gremlins, 1984

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

Pink bell bottoms, pink platforms and her pink Volvo (1973)
Michelle Pfeiffer, 1991.
Debbie Reynolds with a Stanley cup, 1951

Dad: Let’s take a picture that will make Mom angry, 1970
Jerry Stiller back in the day, 1974.
Phoebe Cates on set during “Fast Times at Ridgemont High” shoot, 1981

Marlon Brando and photographer Mary Ellen Mark, 1970s

First day in school for Mila Kunis, 1980’s.
Enjoying cocktails in the 1970s.

A wedding in 1949.
Lynda Carter as a blonde in ‘The New Original Wonder Woman (1975)

Lynda Carter in her iconic blue Wonder Woman scuba suit, 1977

Lynda Carter representing Arizona at the Miss World USA 1972

Albert Einstein at the Beach, 1939.
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

Carrie Fisher in New York, 1980

Farrah Fawcett, Kate Jackson, & Jaclyn Smith, 1976

Jayne Mansfield, 1960

Alicia Silverstone with her grandpa, Sydney, at her Bat Mitzvah (1989)

Sally Fields, 1970s

Sandra Bullock, 1990s

Rose Byrne and Heath Ledger, 1999

Anita Ekberg, 1950s

Betty White in 1948

Debbie Reynolds and baby Carrie Fisher, 1959
Winona Ryder, Jodie Foster and Julia Roberts in 1989

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

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

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

Michael Jackson, 1980s

Willie Nelson in 1960

Keanu Reeves, 1990s

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
The employee cafeteria at Disneyland, 1961.

Prince, 17

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.

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 stylish family outing in 1946.

David Lee Roth and his signature leap circa 1982

Valerie Bertinelli and Eddie Van Halen getting married in 1981

Raquel Welch

Marilyn Monroe photographed by Sam Shaw. Plaza Hotel, New York (1957)

Robert Downey jr at the academy awards 1993

Jayne Mansfield, 1950s
Marilyn Monroe photographed by Bruno Bernard at Racquet Club Resort Hotel in Palm Springs, 1949.
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

Johnny Cash eating cake in a bush, 1971.

Clara Bow, 1927
Meryl Streep, 1982

A young Agatha Christie.

Gillian Anderson, 1990’s

Cameron Diaz and Jim Carrey at Cannes Festival, 1994

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

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

Mike Tyson playing Punch Out, NES • 1987
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.

Meryl Streep, 1988

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

Richard O’Brien and Tim Curry Circa 1974

Stevie Nicks working on Rumours, 1976

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

Waylon Jennings and Johnny Cash
Dolly Parton, live late ’60’s
Dustin Hoffman and Jon Voight in Midnight Cowboy, 1969.

Seventeen-year-old Elizabeth Taylor washing her golden cocker spaniel.
Vivian Leigh in ‘Caesar and Cleopatra,’ 1945.
Dean Martin, Kirk Douglas, Jimmy Durante, and Tony Curtis at a Friars Club event, in the late 1950s.

Joan Fontaine and Laurence Olivier in Rebecca, 1940.

Paul Newman in Cool Hand Luke, 1967.

Ingrid Bergman and her daughter Isabella Rossellini.
Hank Aaron Mobile, Alabama 1974, a week before he broke Ruth’s home run record.

Elizabeth Taylor being dramatic at a boxing match in 1960.
Audrey Hepburn in My Fair Lady, 1964.

Gene Hackman in “The French Connection” (1971)

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

Jamie Lee Curtis and Christopher Guest were married on December 18, 1984.

Alma Reville with the prop head of her husband, Alfred Hitchcock, 1972.
Gregory Peck and Brock Peters in To Kill a Mockingbird, 1962.

Jessica Tandy, 1949
Vivien Leigh behind the scenes of Gone with the Wind, 1939.

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

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

British raver girls partying in Ibiza, 1999
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.

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.

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

Leonardo DiCaprio, Johnny Depp, and Brad Pitt.
Marilyn Monroe surrounded by fan mail, 1955. Photo by Slim Aarons.

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

Ali getting distracted by Iris in an exhibition match against local boxer Cholito. Puerto Rico, 1976

Lynda Carter, 1970s

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

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

Shirley MacLaine with her brother, Warren Beatty in 1942.

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

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

Michelle Pfeiffer, early 1980s

Lynda Carter at the Century Plaza Hotel in Los Angeles, 1977
Joni Mitchell playing guitar for Eric Clapton and David Crosby, 1968

Linda Blair with Black Sabbath, 1976.

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

Robin Williams street performing in New York City, 1979.

Lunch at the Universal studio commissary, 1963.

Debbie Reynolds and Carrie Fisher, 1961

Andre the Giant holding up NFL quarterback Joe Theismann, 1975

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

Lynda Carter, licking an ice cream cone in the 1960s

Miss Idaho Potato, 1935

Carrie Fisher and her mom, Debbie Reynolds i,n 1972

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

Sophia Loren in “Two Nights With Cleopatra” (1954)

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

Changing stations on the beach. 1930s

A woman and dogs spotted in Los Angeles, 1970.

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

Sir Ian McKellen in London, 1969

Barry Gibb of The Bee Gees receiving an award from actress Tsai Chin after being voted best dressed pop star, London, July 12th 1969 

Brian May, 1963

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

Debbie Reynolds and Carrie Fisher, 1974

A vintage selfie from 1934

Filming Hey Jude, Twickenham Studios, London. September 1968.

Burt Lancaster and Audrey Hepburn in The Unforgiven, 1960.

Meryl Streep photographed by Henry Wolf in 1979.

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

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.

Hunter S. Thompson and Oscar Zeta Acosta at Caesar’s Palace, 1971

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

Danish model Winnie Holman. Cannes, 1975 – by Helmut Newton.

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.

Audrey Hepburn arrives at London Airport in 1953.

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

Joanne Woodward and Paul Newman, 1958.

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

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

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

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

Elizabeth Taylor with her mother.

Joanne Woodward and Paul Newman relaxing at home.

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

Laurence Olivier and Vivien Leigh.

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

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

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

Marilyn Monroe visting a wounded soldier in Japan, 1954

Natalie Wood (1960s)

1985 trailer park family

Actress and singer Donna Loren kissing Burt Ward on ‘Batman’ (1966)

Actress Joan Bradshaw walking her poodle around the Hollywood Blv. and Vine Street intersection, 8 of September of 1957.

Anna Kashfi, 1956, in an Indian sari (Marlon Brando’s first ex-wife)

Anna Nicole Smith (1990s)

Anthony Hopkins and Jodie Foster in 1996.

Bette Davis and Joan Crawford in What Ever Happened to Baby Jane? (1962)

Big Trouble in Little China (1986) 

Michael Jackson and Madonna at the 1991 Oscars 
Heather Graham 1988

Pope Francis in 1998 on public transport in Buenos Aires

Ex Soviet Navy sailor with his girlfriend. Photo by Lucien Perkins, Gorky Park, Moscow, Russia, 1993. 

Ernest Hemingway, Alec Guinness, and Noel Coward in Havana, 1959. 

JFK and Jackie on their wedding day, Sept 12, 1953, in Newport, RI.

Monica Bellucci photographed by Jean-Marie Marion, 1997

Pizza Hut back in the 1990s.

Demi Moore (1990s)

Family on a camping trip in the Canadian Rockies 1970

14-year-old Bryan Cranston in 1970.

Paul McCartney, pictured in 1970 by his wife Linda McCartney, the same year as the breakup of The Beatles.

A young couple in Chicago, 1975
Arnold Schwarzenegger meeting his fans in Moscow, 1988
Jacqueline Bisset (1973)

Monica Bellucci with her motorcycle, 1990s
Steven Spielberg and Jeff Cohen aka “Chunk” on set of ‘The Goonies’ in 1986

Brigitte Bardot

Sophia Loren in Naples, Italy, 1961.
Cameron Diaz

1963 Chevrolet Corvette Split Window.
Sally Field at age 19, 1966

Turkey Hunt 1950 Publicity Photo Shoot With Marilyn Monroe

Marilyn Monroe in How To Marry A Millionaire (1953)
Alicia Witt at the 1998 premiere of Urban Legend

Unknown model in 1936.

Fitness figure Kellie Everts a little before the Miss Olympia contest, 1980.

Marilyn Monroe posing with Clark Gable during their free time filming “The Misfits”, circa 1960.

Jack Nicholson with his daughter Jennifer in the 60s

Rare Candid Photos of Marilyn Monroe with a Mountie, in Banff National Park, Alberta, Canada in 1953.
Lady Miss Kier, singer of Deee-Lite in the 90s

Lana Turner at a nightclub wearing a veiled hat and fishnet gloves in 1940s. Her jealous boyfriend Johnny Stompanato once threatened Sean Connery with a gun, leading Connery to knock him out.
Helen Mirren in Herostratus (1967)

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