Every actor has to start somewhere. For Robert Redford, that meant an uncredited role as a basketball player in the 1960 romantic comedy Tall Story, which also served as a satirical look at how colleges were in truth marriage factories. The main leads were Anthony Perkins and Jane Fonda in her feature film debut. The movie failed to wow audiences and critics but led to a long and prolific friendship between Redford and Fonda, both off- and onscreen.

Redford became a bonafide leading man when co-starring opposite Fonda again in 1967’s Barefoot in the Park, the movie adaptation of Neil Simon’s Broadway play exploring the more comical side of the cultural revolution of the 1960s. Redford’s character is an uptight lawyer who marries a free-spirited young woman perfectly content with life in their five-floor New York City walk-up apartment (the same can’t be said for her new spouse). The pic was a commercial hit, earning $30 million at the box office against a $5 million budget, not adjusted for inflation.

Robert Redford and Paul Newman’s seminal Western about two outlaws on the run was the top-grossing film of 1969 on its way to earning a slew of top Oscar nominations, including for best picture and best director (George Roy Hill). Wins included best song for the iconic tune “Raindrops Keep Falling on My Head.” The film was of profound personal importance to Redford — he used his character’s name, the Sundance Kid, when coming up with the name for the Sundance Film Festival.

With Redford’s star status on the rise, Paramount Pictures chief Robert Evans enticed him to appear in two movies directed by Roman Polanski: Rosemary’s Baby and skiing sports drama Downhill Racer. Ultimately, Polanski walked away from Downhill Racer, while Redford put the brakes on starring in Rosemary’s Baby. Evans was none too happy, but Redford was determined make Downhill Racer and ultimately hit the slopes with director Michael Ritchie. The 1969 film may have stumbled at the box office — it didn’t help that it opened only a month after Butch Cassidy and the Sundance Kid — but it did earn praise from Roger Ebert, who called it “the best movie ever made about sports — without really being about sports at all.”

Long before Leonado DiCaprio starred in The Revenant, Redford likewise starred as a rugged mountain man trying to survive the wilderness in the 19th century frontier epic Jeremiah Johnson. It was the first Hollywood Western to play at the Cannes Film Festival, as well as marking Redford’s second time working with director Sydney Pollack after 1966’s This Property is Condemned (the two had first met as actors on the set of the 1962 Korean War film, The Hunt, which was Redford’s first credited film acting role). The duo insisted that Jeremiah Johnson be filmed on location in Utah, Redford’s adopted home state. When terrible weather struck, Pollack even mortgaged his home to supplement the budget after Warner Bros. insisted that the cast and crew return to L.A. and use the backlot.

The political dramedy was among a number of films Redford made throughout his career — whether as a director or actor or both — that touched upon the intersection of politics and corruption. He always said the film, which was directed by Downhill Racer‘s Michael Ritchie — was a labor of love in telling the tale of an idealistic young man and son of a former Democratic governor who is persuaded by a determined campaign manager (Peter Boyle) that he can win a California senatorial race by telling the truth. Things, of course, don’t go exactly as planned, and the protagonist is slowly compromised. The film earned Jeremy Larner an Oscar for best screenplay.

For certain generations, The Way We Were is considered one of the best romantic dramas of all time and ranked No. 6 on AFI’s 100 Years … 100 Passions survey. Director Sydney Pollack and the movie’s stars, Redford and Barbra Streisand, were a formidable trifecta in bringing to life a love story spanning several decades that also tried to double as a history lesson into the perils facing post-World War II America, including the rise of McCarthyism and ongoing antisemitism and racism (a number of prominent movie critics said the movie didn’t go far enough). Audiences didn’t seem to mind, while Academy voters bestowed Streisand with a best actress Oscar nomination. The movie also won the Oscar for best original song for “The Way We Were” (both the theme song and the soundtrack stayed high up on Billboard’s top charts for months). Released in the fall of 1973 — when Redford was considered one of the sexiest men alive, a distinction he always winced at — The Way We Were grossed an astonishing $45 million-plus in the U.S., not adjusted for inflation.

Audiences lined up around the block to see Redford and Newman reunite on the big screen for the first time since Butch Cassidy nearly a decade earlier. To boot, George Roy Hill had returned to direct. The period caper pic, set in 1936, was both a box office sensation and critical hit. And it was a big winner at the 46th Academy Awards, winning seven of its 10 Oscar nominations, including best picture, best director, best original screenplay and best film editing (Redford was nominated for best actor but didn’t win). In 2004, the film was selected for preservation by the Library of Congress’ U.S National Film Registry. Over the course of its life, The Sting has grossed north of $155 million at the domestic box office and another $100 million overseas, according to Box Office Mojo.

After a string of wins, Redford got a taste of what can go wrong when a project is troubled, such as Paramount’s 1974 version of The Great Gatsby. Truman Capote took a pass at the first script for studio chief Bob Evans but was later replaced by Frances Ford Coppola. (Redford vouched for Coppola based on a rewrite he’d done of The Way We Were.) Redford, who lobbied hard for the iconic role, starred opposite Mia Farrow in the film, which didn’t go over well with critics. Based on 41 reviews collected by Rotten Tomatoes, the rating is a dismal 41 percent. Financially, however, the movie wasn’t an entire disaster, earning $26 million at the box office against a reported $7 million budget.

Pollack directed Redford for a second time in this spy thriller, which may not have blown up at the box office but has had a lasting cultural impact. The movie stars Redford as a nerdy (no joke) CIA researcher whose office in New York is overcome with intruders who murder all of his colleagues while he’s at lunch. In turn he takes a woman hostage, played by Faye Dunaway, while figuring out a plan of attack from the safety of her apartment. Three Days of the Condor, released in September 1975, earned a solid $28 million domestically, not adjusted for inflation. Decades later, the movie is credited with helping to inspire Marvel’s Captain America: The Winter Soldier, while lines from the film were also referenced in Seinfeld.

Talk about serendipity. When Redford was promoting The Candidate in 1972 and waiting to start shooting The Way We Were, he became obsessed with Bob Woodward and Carl Bernstein’s stories for The Washington Post on the Watergate break-in. That fall, he reached out to Woodward personally, long before anyone knew the magnitude of what would unfold. Redford’s persistence paid off. Two years later, he secured the movie rights to Woodward and Bernstein’s book of the same name for $450,000 amid President Richard Nixon’s resignation in 1974. Warner Bros. came aboard and agreed to finance the film for $8.5 million, with Redford cast as Woodward and Dustin Hoffman as Bernstein. Directed by Alan J. Pakula, the film was among the top five grossing movies of year on its way to being nominated for best picture and best director, among other categories. It’s picked up numerous other accolades through the years.

While it’s hard to believe, Redford never earned an Oscar for any of his onscreen roles, but he did take home a best director trophy for Ordinary People, his feature directorial debut. The film follows a family dealing with the fallout of the death of the eldest son, with Donald Sutherland, Mary Tyler Moore and Timothy Hutton (who earned an Oscar for his performance) playing the Jaretts. Redford was awarded an honorary Oscar in 2001 for his achievements in film.

Redford had taken a three-year break from acting when signing on to star in the Barry Levinson-directed sports drama The Natural, which marked the first release from Sony’s Tri-Star Pictures. The movie also teamed Redford with Glenn Close for the first time. Inspired by Bernard Malamud’s 1952 novel of the same name, the film revolves around the life and career of Roy Hobbs, a baseball player graced with what’s referred to as “natural” talent. The Natural was generally well-received by audiences and critics, although some took great issue with changing the book’s ending in order to end the movie on a lighter note. The Natural earned nearly $48 million at the U.S. box office to land at No. 14 on the list of the year’s top earners, and was nominated for four Academy Awards, including best supporting actress for Close.

The sweeping romantic epic reunited Redford with director Sydney Pollack for the fifth time, so they had their routine down. But it was only the first time he worked with Meryl Streep, yet the onscreen chemistry between them, combined with the sweeping views of Nairobi’s countryside, propelled the period movie to earn $85 million domestically and $225.5 million globally. Times were changing and Hollywood studios was starting to see big returns from the foreign box office. Out of Africa all but swept the Oscars, including wins for best picture, best director and best cinematography. Streep was nominated, but didn’t prevail, for her performance as the real-life Danish author Karen Blixen, whose 1937 memoir Out of Africa was the inspiration for the movie (she penned the book under the pseudonym Isak Dinesen).

A billionaire (Redford) offers a young married couple (Demi Moore and Woody Harrelson) $1 million for the wife to spend a night with him. While the reviews were far from the best of Redford’s career (the film was largely panned by critics), Indecent Proposal became a hit with audiences, grossing $266 million at the worldwide box office.

In his career, Redford seemed to have tackled every genre of filmmaking — from comedy to romance to drama to Western and beyond — so it only made sense that the actor would also tackle superhero films. As U.S. government leader and secret Hydra operative Alexander Pierce, he brought gravitas to the Marvel Cinematic Universe. His character made a small cameo in Avengers: Endgame.

Redford’s final film was a perfect capstone for a career of playing charming delinquents and rakish outlaws. The David Lowery movie tells the sort of true story of Forrest Tucker, a 70-something career criminal who, after an escape from San Quentin, goes on a string of bank heists. Prior to the film’s release, Redford indicated that The Old Man & The Gun would be his last feature. He said at the time, “I think it was a mistake to say that this was my last film because I think I just could’ve quietly slipped out of acting and into a new category.”