By Wonderwall.com Editors
9:34pm PDT, Sep 16, 2025
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Take a look back at some of Hollywood's most beloved now-mature leading men in the early days of their careers, starting with an Oscar winner who just
died at 89 on September 16, 2025…
Robert Redford was giving us major Brad Pitt vibes — in the best way possible — in this photo from 1973's "The Way We Were" when he was in his mid-30s.
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So nice we included him twice! Blonde, blue-eyed matinee idol Robert Redford was a handsome devil in this publicity photo taken for his 1966 film "This Property is Condemned." The movie, which is based on the play by Tennessee Williams, hit theaters when the actor was 29.
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Kids these day might not understand why Johnny Depp was once considered the hottest man in Hollywood. Well, just look at those cheekbones circa 1990 when he starred in "Cry-Baby" at 26.
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"Indiana Jones" and "Star Wars" franchise hunk Harrison Ford (seen here in an early publicity shot from the late '60s or early '70s) was a stone cold fox when he started his career in Hollywood.
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Back in the day, Al Pacino was a total stud. He had a handsome-meets-broody thing going on in the 1971 drama "Panic in Needle Park."
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George Clooney has been a handsome devil for decades. He's seen here as George Burnett on "The Facts of Life" in 1985 when he was 24.
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We love this smoldering shot of "Yellowstone" star Kevin Costner, who was in his mid-30s when he posed for this photo on the set of his 1990 film "Revenge."
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When Brad Pitt appeared opposite Geena Davis in 1991's "Thelma & Louise" — which debuted when he was 26 — he solidified himself as a Hollywood heartthrob for decades to come.
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Look at this young hunk in "Coal Miner's Daughter" back in 1980! A babyfaced Tommy Lee Jones, then 34, donned a cowboy hat in this still from the film.
Fourteen years later, he won an Oscar for his work in "The Fugitive."
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John Travolta — seen here as a young man in the early '70s — shot to fame in 1975 when he began starring on the hit TV show "Welcome Back, Kotter," then solidified his star status with major roles in the latter half of the decade in projects including the TV movie "The Boy in the Plastic Bubble" and films like "Carrie," "Grease" and "Saturday Night Fever."
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Ryan O'Neal — who died at 82 on Dec. 8, 2023 — found fame in his early 20s when he began a five-year tenure on the hit TV series "Peyton Place." (He's seen here as Rodney Harrington on the popular primetime soap opera in 1967.) He went on to deliver an Oscar-nominated performance opposite Ali MacGraw in the film "Love Story," then made more notable movies including "Paper Moon" and "Barry Lyndon."
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Those eyes! That hair! Alec Baldwin looked gorgeous — and a little Ryan Gosling-esque — on the set of nighttime drama "Knots Landing" in 1985.
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Hello, Christopher Walken! The Oscar-winning "The Deer Hunter" actor wasn't always known for his crazy hair and wild eyes. He was just crazy good-looking back in 1969 when he appeared in a production of Tom Stoppard's play "Rosencrantz and Guildenstern Are Dead" when he was in his mid-20s.
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Well, hello there, Jeff Bridges. The actor gave off some serious Hemsworth brothers vibes with his look in 1984's "Against All Odds."
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Robert De Niro — who welcomed his seventh child in 2023 — was lookin' good in 1971's "The Gang That Couldn't Shoot Straight" when he was in his late 20s.
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After you've seen this still of Jack Nicholson in 1963's "The Raven" when he was in his mid-20s, you'll understand why his list of alleged romantic conquests includes Anjelica Huston, Michelle Phillips, Janice Dickinson, Lara Flynn Boyle, Rita Moreno, first lady of Canada Margaret Trudeau, Angie Everhart, Julie Delpy, Joni Mitchell, Marg Helgenberger and Kate Moss.
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Sir Michael Caine — who's seen here in a portrait taken circa 1966, the same year he starred in the hit movie "Alfie" while he was in his early 30s — recently retired: In October 2023, the English actor announced that at 90 — following the release of his final film, "The Great Escaper," the same month — he's stepping back from movie-making. "I keep saying I'm going to retire. Well, I am now," the two-time Oscar winner said on BBC Radio 4's "Today" show. "I've figured, I've had a picture where I've played the lead and it's got incredible reviews. The only parts I'm likely to get now are old men … and I thought, well, I might as well leave with all this — what have I got to do to beat this?"
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Richard Gere has always been incredibly good-looking. The "Pretty Woman" and "An Officer and a Gentleman" star looks like a total hunk in this still from 1977's "Looking for Mr. Goodbar" that was taken when he was in his late 20s.
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"Batman" and "Beetlejuice" star Michael Keaton started acting in the mid-'70s and got his big break on the 1979 TV comedy "Working Stiffs" — he's seen here in a promo for the CBS show when he was 28 — which led to a starring role in the hit comedy "Night Shift" (and so much more!).
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Clint Eastwood was a total hunk back in the day. He's seen here at 25 in 1955, the same year he made his big screen debut. Yowza!
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Yes, James Bond actor Pierce Brosnan has always been gorgeous. He certainly looked dapper in a promotional photo for his hit show "Remington Steele" back in the '80s.
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That smirk! "Die Hard" action star Bruce Willis is seen here back when he was playing Blue Moon Detective Agency investigator David Addison on the hit ABC series "Moonlighting" in 1986 when he was 31.
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Kurt Russell was a handsome young man in his mid-20s when he portrayed Morgan Beaudine on the TV show "The Quest" in 1976.
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Mel Gibson launched his acting career back in the late '70s, but he's been through so much since then that we often forget how he became such a huge star in the first place. Here's a reminder: Once upon a time — specifically when he was in his mid-20s in 1981's "Gallipoli" — the controversy-sparking actor was a total hunk.
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Today, many people might know him best as the voice of Darth Vader in the "Star Wars" films, but James Earl Jones looked H-O-T opposite Diana Sands in 1963's "East Side/West Side."
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Tom Hanks was hilarious — and quite handsome — when he starred in the 1965 comedy "Volunteers." He's seen here in a promotional photo for the flick, which hit theaters when he was in his late 20s.
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Let's be honest: Denzel Washington has always been a dreamboat! He's seen here in character as Dr. Philip Chandler on the first season of the hit medical drama "St. Elsewhere" in 1982 when he was in his late 20s. During that decade, the future Academy Award winner appeared in films like "Carbon Copy," "Power," "Cry Freedom" and "Glory."
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Swoon! Now we know why a young Warren Beatty broke so many hearts early in his Hollywood career.
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The late Val Kilmer (and his cheekbones!) had movie fans swooning when he played hotshot Navy pilot Iceman in the 1986 film "Top Gun." He was in his mid-20s at the time.
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James Caan — the movie star with a tough-guy persona who starred in "The Godfather," "Misery," "Elf" and more — died at 82 on July 6, 2022. He's seen here as a handsome young man in his late 20s in 1968.
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Don Johnson smoldered in a promotional photo for NBC's "Miami Vice" in 1984.
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The late Sidney Poitier, who died at 94 in January 2022, posed for this portrait taken circa 1960 — four years before he won the Oscar for his work in "Lilies of the Field," making him the first Black actor to take home a competitive Academy Award.
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Mark Harmon has always been such a handsome man! In 1986's "Let's Get Harry," the "NCIS" star looked super-suave. That smolder!
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Liam Neeson has always been a total heartthrob! The Northern Irish actor, seen here in 1988 when he was in his mid-20s, was a hunk long before we fell for him in films like "Love Actually" and "Taken."
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It's been nearly five long decades since Nick Nolte starred in 1977's "The Deep." If only we could turn back time!
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Well, hello there! Former gymnast and professional dancer Mads Mikkelsen found fame in his native Denmark with his acting work in 1996's "Pusher" and global fame a decade later when he played a villain in the 2006 James Bond film "Casino Royale." A decade after that, he starred as Dr. Hannibal Lecter on TV (to rave reviews!) and in 2022 took on yet another villain: dark wizard Gellert Grindelwald in "Fantastic Beasts: The Secrets of Dumbledore." Mads and his cheekbones are seen here back in 2003 at the Sundance Film Festival.
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We've always wondered how Jon Voight spawned the beauty that is Angelina Jolie. After taking a look back at him in 1969's "Midnight Cowboy," we finally get it.
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Howdy, cowboy! Tom Selleck raised temperatures on 1982's "The Shadow Riders."
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Let's just say Sean Connery wasn't cast to portray James Bond throughout the '60s because he was bad-looking. Here he is in 1957's "Hell Drivers."
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The 1986 movie "Matador" showcased Spanish actor Antonio Banderas's youthful good looks as well as his talent.
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Mr. Feeny, is that you?! Before he charmed viewers as the lovable teacher on "Boy Meets World," William Daniels was a heartbreaker! He's seen here in 1965.
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Back in 1975, Chevy Chase looked like the sauce yet silly love child of Harrison Ford and Andy Samberg. Yum!
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Get a load of Martin Sheen opposite Sissy Spacek in 1973's "Badlands." He looks like James Dean, no?
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Dick Van Dyke is seen here circa 1963 when he was starring on "The Dick Van Dyke Show" in his 30s. He'd just won a Tony Award for his work in the Broadway musical "Bye Bye Birdie" and a year later starred in the classic children's film "Mary Poppins."
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Danny Glover sure looked handsome when he starred in "The Color Purple" in 1985.
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How cute was John Slattery in the '90s? The "Mad Men" and "Sex and the City" silver fox is pictured here filming an episode of the series "Under Cover" in 1990. From his adorable round specs to his curly dark hair, what's not to love?
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There was a time when Dustin Hoffman was thought to be one of the hunkiest men in Hollywood. Considering the way he looks in the iconic 1972 film "The Graduate," we definitely understand why.
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William Shatner might be more silly than sauve these days, but there's a reason Captain Kirk was such a hit with the ladies!
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Whoa! Kevin Bacon was so young and handsome when he starred in 1984's "Footloose."
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Nearly 20 years before he won an Oscar for "The Silence of the Lambs," Welsh actor Anthony Hopkins looked young and handsome as he posed for a portrait in 1971 — just a few years after he made a name for himself on the London stage and in the film "The Lion in Winter."
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We've absolutely adored Ian McKellen for a while now — even before we realized that back in 1974, he looked like this!
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In addition to being a total inspiration, Sylvester Stallone was also a brooding hunk early in his career. When "Rocky" debuted in 1976, the world got its first dose of the multi-talented actor.
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Another undisputed '80s heartthrob? None other than Perry King. Best known for his work on the series "Riptide" and in the film "The Hasty Heart," for which he earned a Golden Globe nomination, Perry's suave look made audiences swoon.
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"Dirty Dancing" star Patrick Swayze was undeniably talented and handsome — it's no wonder the "Ghost" star was one of Hollywood's most beloved romantic leads.
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If only Mickey Rourke hadn't sustained injuries to his face during his stint as a professional boxer during the early '90s, he might still look like he did in 1986's "9 1/2 Weeks."
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When we think rom-com, we think Hugh Grant. The English actor, who scored leading roles in notable romantic films like "Notting Hill" and "Bridget Jones's Diary," looked as charming as ever in 1994's "Four Weddings and A Funeral."
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A total hunk! Tony Leung — who delivered some incredible moves in his fight scenes as the villain in the 2021 Marvel flick "Shang-Chi and the Legend of the Ten Rings" — looked handsome as a younger man in 2000's "In The Mood For Love."
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Back when he was a young man, Gary Oldman let loose his inner hipster in 1988's "We Think the World of You." And we liked it!
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It's been more than 30 years since we saw Daniel Day-Lewis in the 1988 film "Stars and Bars." The acclaimed actor was certainly easy on the eyes!
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We're not gonna lie: We've always had a crush on Benicio Del Toro. After seeing this pic of him as a young James Bond villain in 1989's "License to Kill," you'll understand why!
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Gerard Butler, you handsome Scottish devil! The "300" star is seen here back in 1999 when he was on the TV show "Lucy Sullivan is Getting Married."
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So handsome! Before he captured our hearts as Tony Stark, Robert Downey Jr. looked like the ultimate bad boy. He's seen here in 1987's "Less Than Zero."
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While comedian Jon Stewart definitely looks good sporting silver hair nowadays, there was once a time when he rocked luscious brown locks. Pictured here at the premiere of "The Waterboy" in 1998, John looked super-handsome — and stylish!
