Share Tweet Pin Email By Wonderwall.com Editors 9:34pm PDT, Sep 16, 2025 _ 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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MORE: Follow Wonderwall on MSN for more top news and photo galleries _ 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. _ 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. _ "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. _ 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." _ 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. _ 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." _ 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. _ 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." _ 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." _ 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." _ Those eyes! That hair! Alec Baldwin looked gorgeous - and a little Ryan Gosling-esque - on the set of nighttime drama "Knots Landing" in 1985. _ 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. _ Well, hello there, Jeff Bridges. The actor gave off some serious Hemsworth brothers vibes with his look in 1984's "Against All Odds." _ 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. _ 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. _ 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?" _ 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. _ "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 l