John Cusack Then & Now: Photos Of The ‘Say Anything’ Star To Mark His 56th Birthday

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June 28, 2023 6:04PM EDT

Celebrate beloved actor John Cusack’s birthday with a look at photos from his young days to now.

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John Cusack: Then & Now

John Cusack: Then & Now — John Cusack, born June 28, 1966, is an American actor, producer, screenwriter, and political activist.

Born into Hollywood as the son of filmmaker Dick Cusack, John began in 1980s coming-of-age dramedies such as ‘Sixteen Candles’, (1984) ‘The Sure Thing’ (1985), ‘Better Off Dead’ (1985), and ‘Say Anything…’ (1989).

He turned to darker indie roles in the late 80s and 90s, appearing in ‘Eight Men Out’ (1988), ‘The Grifters’ (1990), ‘True Colors’ (1991), and ‘Bullets Over Broadway’ (1994). Other prominent roles include ‘Grosse Pointe Blank’ (1997), ‘Con Air’ (1997), ‘Anastasia’ (1997), ‘Being John Malkovich’ (1999), and the romantic comedies ‘High Fidelity’ (2000), ‘America’s Sweethearts’ (2001), ‘Serendipity’ (2001), and ‘Must Love Dogs’ (2005).

John Cusack has had such an incredible career. Here, he appears in ‘Better Off Dead’. The teen comedy was about a boy who tries to unsuccessfully end his life, so hilarious result.

Want to learn more about John Cusack’s career? Look no further than our gallery here.

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‘The Sure Thing’

‘The Sure Thing’ — John Cusack appears in ‘The Sure Thing’. The 1985 flick is about a college kid trying to get lucky in California.

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‘Hot Pursuit’

‘Hot Pursuit’ — John Cusack looks rugged in 1987’s ‘Hot Pursuit’. The movie was a comedy of errors about a guy trying to meet his girlfriend in the Caribbean.

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John Cusack In 1989

John Cusack In 1989 — John Cusack looks dapper in this photo from 1989. He wore a trench coat and tie.

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‘Say Anything’

‘Say Anything’ — John Cusack appears in the iconic boombox scene in the 1989 Cameron Crowe movie ‘Say Anything’. The teen romance follows the relationship between Lloyd Dobler (John Cusack), an average student, and Diane Court (Ione Skye), the class valedictorian.

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‘Money For Nothing’

‘Money For Nothing’ — John Cusack appears in ‘Money For Nothing’. The 1993 crime comedy was about an unemployed man who finds a money bag of $1.2 million after it was dropped by an armored car.

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‘This Is My Father’

‘This Is My Father’ — John Cusack appears in 1998’s ‘This Is My Father’. He was part of the supporting cast.

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‘Being John Malkovich’

‘Being John Malkovich’ — John Cusack is in the 1999 Spike Jonze film ‘Being John Malkovich’. The absurd comedy was about a puppeteer who discovers a portal that leads literally into the head of movie star John Malkovich.

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‘America’s Sweethearts’

‘America’s Sweethearts’ — John Cusack starred in 2001’s ‘America’s Sweethearts’. The film, which also starred Billy Crystqal, Julia Roberts and Catherine Zeta-Jones, was about a movie publicist dealing with the messy public split of his movie’s co-stars. Meanwhile, he tries to keep reporters at bay while a reclusive director holds the film’s print hostage.

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John Cusack In 2005

John Cusack In 2005 — John Cusack is all smiles at the premiere of ‘The Ice Harvest’ in Nov. of 2005. The event was in Chicago.

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‘War, Inc’

‘War, Inc’ — John Cusack has killer instincts in 2008’s ‘War, Inc.’ The action-comedy was about a corporation that hires a professional assassin to pose as its trade show representative. He is tasked to organize the wedding of a Middle Eastern pop star so he can get the opportunity to kill a Middle Eastern politician.

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‘Hot Tub Time Machine’

‘Hot Tub Time Machine’ — Blast from the past! Clark Duke, Craig Robinson, John Cusack, and Rob Corddry (left to right) appear in the 2010 sci-fi comedy ‘Hot Tub Time Machine.

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John Cusack At The 2014 Cannes Film Festival

John Cusack At The 2014 Cannes Film Festival — John Cusack gives the crowd a point during a photocall for the fil ‘Maps to the Stars’ at the 67th Cannes Film Festival in France on May 19, 2014.

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John Cusack In 2017

John Cusack In 2017 — John Cusack attends a speaking series in honor of Harry Belafonte in Chicago on Feb. 10, 2017. He wore all black.

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John Cusack In 2019

John Cusack In 2019 — John Cusack listens to questions during a Q&A at a Fort Lauderdale, Florida screening of ‘Say Anything’ in Jul. of 2019. He wore a baseball cap and a jacket.

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‘Utopia’

‘Utopia’ — Paradise lost! Hadley Robinson, John Cusack, and Cory Michael Smith (left to right) appear in season 1 of ‘Utopia’ in 2020. The show was about a group of young adults, who meet online and get a hold of a cult underground graphic novel, which not only pins them as a target of a shadowy deep state organization, but also burdens them with the dangerous task of saving the world.

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