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Looking Back At Bruce Willis’ Most Iconic Roles From Over The Years

Photo Credit: murraymomo / Twentieth Century Fox / MovieStillsDB
Photo Credit: murraymomo / Twentieth Century Fox / MovieStillsDB

In early 2022, Bruce Willis’ family announced his retirement, sharing he’s been diagnosed with aphasia, a disease that affects a person’s ability to speak, write and understand language – both verbal and written. His family was dealt another blow in early 2023, announcing the actor’s condition had worsened and that he’d been diagnosised with frontotemporal dementia (FTD), for which there is no treatment.

One month later, Willis turned 68. His wife, Emma, published an emotional post about the grief the family felt on his birthday, speaking candidly in the Instagram video. “Today is my husband’s birthday. I have started the morning by crying, as you can see by my swollen eyes and snotty nose,” she said. “I just think it’s important that you see all sides of this.”

“I do have times of sadness, every day,” she added. “Grief, every day. And I’m really feeling it today on his birthday.” In a second post, she wrote, “My birthday wish for Bruce is that you continue to keep him in your prayers and highest vibrations because his sensitive Pisces soul will feel it. Thank you so much for loving and caring for him too.”

Fellow action star Arnold Schwarzenegger has since commented on Willis’ condition, calling him “a kind man” and “a huge, huge star.” A long-time fan of Willis, Schwarzenegger said, “I think that he’s fantastic. He was, always for years and years, a huge, huge star. And I think that he will always be remembered as a great, great star. And a kind man.”

He continued, “I understand that under his circumstances, health-wise, that he had to retire. But, in general, you know, we never really retire. Action heroes, they reload.”

To honor Willis’ illustrious and decades-spanning career, we thought we’d take a look at our favorite movie and television roles of his. (Warning – spoilers ahead!)

Die Hard (1988)

Bruce Willis as John McClane in 'Die Hard'
Die Hard, 1988. (Photo Credit: Triton / Twentieth Century Fox / MovieStillsDB)

Once again, we will ask the age-old question: Is Die Hard (1988) a Christmas movie? We say no, because we love to watch it all year long! This is arguably Bruce Willis’ most famous movie.

He plays NYPD police officer John McClane, who goes on a trip to visit his wife and children in Los Angeles. During a Christmas party at his wife’s workplace, several people are taken hostage. McClane quickly realizes he’s the group’s only hope.

What’s so great about the film is that John McClane is relatable; he’s a vulnerable and sometimes error-prone hero. Die Hard is widely considered one of the greatest action movies ever made, and is often named one of the greatest Christmas films (although, we still believe it’s an action movie that takes place during Christmas).

The movie was nominated for four Academy Awards, and elevated Bruce Willis to action-hero/leading-man status.

The Sixth Sense (1999)

Haley Joel Osment and Bruce Willis as Cole Sear and Malcolm Crowe in 'The Sixth Sense'
The Sixth Sense, 1999. (Photo Credit: Zayne / Walt Disney Pictures / MovieStillsDB)

We’ll never truly get over the plot twist involving Bruce Willis’s character in The Sixth Sense. This 1999 horror/thriller focuses on a child psychologist named Malcolm Crowe, who’s trying to help his young patient, nine-year-old boy Cole Sear, who claims he can see dead people. Sear tells Crowe that the people he sees don’t realize they’re dead.

Because of his “sixth sense,” Sear is picked on at school. At first, Crowe is skeptical and thinks the boy has some serious mental health issues. However, after spending more time with him, he realizes his patient may actually have the ability to communicate with those beyond the grave.

The Sixth Sense was an international sensation. It was nominated for six Academy Awards, including Best Supporting Actor for Haley Joel Osment, making him the second-youngest performer to ever to be nominated for the award.

Pulp Fiction (1994)

Bruce Willis and Sy Sher as Butch Coolidge and Klondike in 'Pulp Fiction'
Pulp Fiction, 1994. (Photo Credit: kba / Miramax Films / MovieStillsDB)

He might not be the leading man in Pulp Fiction (1994), but Bruce Willis still deserves a major shoutout for his role as boxer Butch Coolidge. The film weaves interlocking stories of crime in Los Angeles’ underworld during the 1990s, and Coolidge is an aging actor who double-crosses crime boss Marsellus Wallace, played by Ving Rhames.

Willis was already a big name when he scored this role in Pulp Fiction. Director Quentin Tarantino later said the actor made the movie “legit,” even though he wasn’t in a starring role.

Twelve Monkeys (1995)

Brad Pitt and Bruce Willis as Jeffrey Goines and James Cole in 'Twelve Monkies'
Twelve Monkeys, 1995. (Photo Credit: Bane / Universal Studios / MovieStillsDB)

Twelve Monkeys (1995) is a sci-fi film starring Bruce Willis and Brad Pitt. In 1996, an unknown virus wiped out five billion people worldwide. By 2035, the remaining population is forced to live underground.

Willis plays convict James Cole, who agrees to go back to 1990 to earn his parole. When he’s back in 1990, James is placed in a psychiatric facility because no one believes his warnings. While there, he meets psychiatrist Dr. Kathryn Railly (Madeleine Stowe) and patient Jeffrey Goines (Pitt).

In 1996, James kidnaps Railly to have her help with his mission to find the activist group Twelve Monkeys, who are planning on releasing the lethal virus into unknown cities.

Armageddon (1998)

Bruce Willis as Harry S. Stamper in 'Armageddon'
Armageddon, 1998. (Photo Credit: eliks / Touchstone Pictures / MovieStillsDB)

It’s thanks to Armageddon (1998) that we have Aerosmith‘s smash hit, “I Don’t Want to Miss a Thing.”

In the movie, NASA discovers that a huge asteroid is about to collide with Earth in less than a month. Willis plays expert driller Harry S. Stamper, who’s recruited by the space agency to teach astronauts how to drill into the space rock. He shows what it’s like to be a man on a mission while still being a protective father in this memorable role.

Moonrise Kingdom (2012)

Still from 'Moonrise Kingdom'
Moonrise Kingdom, 2012. (Photo Credit: funnymatt1978 / Focus Features / MovieStillsDB)

This might be a more recent movie, but Bruce Willis proves he still has it as he delivers a truly heartwarming performance as Captain Sharp in Moonrise Kingdom (2012).

The year is 1965 when two 12 year olds from the island town of New Penzance fall in love and decide to run away. However, a terrible storm is fast approaching, which forces a group of adults to band together to find the two lovebirds.

Willis plays the loveable police captain heading the search for the two missing preteens. Throughout the film, Captain Sharp seems to be one of the only grown-ups who truly cares about the children’s well-being and overall happiness.

Death Becomes Her (1992)

Bruce Willis and Meryl Streep as Dr. Ernest and Madeline Ashton Menville in 'Death Becomes Her'
Death Becomes Her, 1992. (Photo Credit: GLOWWORM / Universal Studios / MovieStillsDB)

Three legends star in the 1992 satirical comedy, Death Becomes Her: Meryl Streep, Goldie Hawn and Bruce Willis. Streep and Hawn portray rivals fighting for the affection of Willis’s character. The two women decide to drink a magic potion that promises eternal youth and beauty – although, it does cause some unpleasant side effects.

The movie has since acquired a cult following, especially in the LGBTQ+ community.

Moonlighting (1985-89)

Bruce Willis as David Addison in 'Moonlighting'
Moonlighting, 1985-89. (Photo Credit: ansoro / ABC / MovieStillsDB)

Yes, Moonlighting (1985-89) is a television show, but this list wouldn’t be complete without giving his role as David Addison Jr. a shoutout. Bruce Willis won his first Emmy for playing the detective running the City of Angels Detective Agency.

Moonlighting is considered to be one of the first successful examples of a comedy-drama TV series. Similarly, Addison Jr.’s relationship with Maddie Hayes (Cybill Shepherd) is considered one of the best TV couplings of all time.

Friends (1994-2004)

Jennifer Aniston and Bruce Willis as Rachel Greene and Paul Stevens in 'Friends'
Friends, 1994-2004. (Photo Credit: MoviePics1001 / The WB Television Network / MovieStillsDB)

Absolutely no list of Bruce Willis’ greatest acting roles is complete without mentioning his time on Friends (1994-2004). Several different stars had guest roles on the famous sitcom, but none were more iconic than Willis’. He made his appearance in season six, portraying Paul Stevens, the overprotective father of Elizabeth (Alexandra Holden), the much younger girlfriend of Ross Geller (David Schwimmer)

Willis’ cameo was the result of losing a bet. In the spring of 2000, he and Matthew Perry (who played Chandler Bing) co-starred in the movie, The Whole Nine Yards. Perry believed the film would do well at the box office, while Willis thought it would tank. The two decided to make a bet: if it opened at number one, then Willis would have to appear on Friends for free.

More from us: Rita Wilson Explains What Really Happened in That Dramatic Photo From Cannes

Of course, The Whole Nine Yards held the number one spot at the box office for multiple weeks, which resulted in the guest spot. The experience must not have been so bad, though, because Willis won an Emmy for Outstanding Guest Actor in a Comedy Series for the gig.

Madeline Hiltz

Maddy Hiltz is someone who loves all things history. She received her Bachelors of Arts in history and her Master’s of Arts degree in history both from the University of Western Ontario in Canada. Her thesis examined menstrual education in Victorian England. She is passionate about Princess Diana, the Titanic, the Romanovs, and Egypt amongst other things.

In her spare time, Maddy loves playing volleyball, running, walking, and biking, although when she wants to be lazy she loves to read a good thriller. She loves spending quality time with her friends, family, and puppy Luna!