Sydney Pollack was the Oscar winning filmmaker who could’ve branded himself as Hollywood’s favorite journeyman, crafting solid entertainments for over 40 years. But how many of his titles remain classics? Let’s take a look back at all 20 of his films as a director, ranked worst to best.
Born in 1934, Pollack got his start as an actor, studying under legendary New York teacher Sanford Meisner. He cut his teeth is television, appearing in such shows as “The Twilight Zone,” “Playhouse 90” and “Alfred Hitchcock Presents” before transitioning into directing for the small screen. Even after making a name for himself behind the camera, he kept popping up onscreen, starring in “The Player” (1992), “Husbands and Wives” (1992), “Eyes Wide Shut” (1999), “Changing Lanes” (2002), “Michael Clayton” (2007) and his own “Tootsie” (1982), to name but a few.
It was this experience as a performer that made him a favorite with actors, including Robert Redford, with whom he made seven films. He helped guide Jane Fonda, Gig Young and Susannah York (“They Shoot Horses, Don’t They), Barbra Streisand (“The Way We Were”), Paul Newman and Melinda Dillon (“Absence of Malice”), Dustin Hoffman, Jessica Lange and Teri Garr (“Tootsie”), Meryl Streep and Klaus Maria Brandauer (“Out of Africa”) and Holly Hunter (“The Firm”) to Oscar nominations, with Young and Lange winning for their films.
Pollack hit the Oscar jackpot himself with the epic romance “Out of Africa” (1985), which won seven prizes including Best Picture and Best Director for him. Prior to that, he contended for directing “They Shoot Horses, Don’t They?” (1969) and “Tootsie.” As a producer, he competed in Best Picture for “Tootsie,” “Michael Clayton,” and posthumously for “The Reader” (2008).
On the TV side, Pollack won Emmys for directing “Bob Hope Presents the Chrysler Theater” in 1966 and for producing the TV movie “Recount” in 2008 (rewarded posthumously). He competed once again for helming episodes of “Bob Hope Presents” in 1964 and “Bob Casey” in 1963, as well as for producing the “Great Performances” special “James Taylor: Band of One” in 2008.
Tour our photo gallery of Pollack’s 20 films as a director, including some of the titles listed above, as well as “Jeremiah Johnson” (1972), “The Yakuza” (1975), “Three Days of the Condor” (1975) and more.
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20. RANDOM HEARTS (1999)
Image Credit: Columbia Tristar/Kobal/Shutterstock Directed by Sydney Pollack. Screenplay by Kurt Luedtke and Darryl Ponicsan, based on the novel by Warren Adler. Starring Harrison Ford, Kristin Scott Thomas, Charles S. Dutton, Bonnie Hunt, Dennis Haysbert, Sydney Pollack, Richard Jenkins, Paul Guilfoyle.
“Random Hearts” tries to be so many things at once that it fails to be about much of anything at all. It’s a romance about a D.C. internal affairs investigator (Harrison Ford) and a Republican congresswoman (Kristin Scott Thomas) who fall in love after discovering their spouses were having an affair when they’re killed in the same plane crash. It’s also a political drama about Thomas’s half-hearted run for reelection. And it’s a crime thriller about Ford’s hunt for a cop who murdered a witness. Any one of these ideas would’ve made for a terrific movie, but jammed together they create a mess. Pollack shows up as Thomas’s campaign advisor.
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19. CASTLE KEEP (1969)
Image Credit: Columbia/Filmways/Kobal/Shutterstock Directed by Sydney Pollack. Screenplay by Daniel Taradash and David Rayfiel, based on the novel by William Eastlake. Starring Burt Lancaster, Patrick O’Neal, Jean-Pierre Aumont, Scott Wilson, Tony Bill, Astrid Heeren, Al Freeman, Jr., James Patterson, Bruce Dern, Peter Falk.
William Eastlake’s fantastical novel makes a bumpy transition to the big screen in this unbearably pretentious war epic. Burt Lancaster stars as the one-eyed leader of a WWII squadron in the days leading up to the Battle of the Bulge. The ragtag group takes refuge in an ancient Belgian castle, where some truly bizarre things start to test their sanity. A surreal blending of comedy and combat, with some romance thrown in between Lancaster and the beautiful Countess (Astrid Heeren) whose husband (Jean-Pierre Aumont) wants him to sire an heir with her. A waste of a talented cast, including scene-stealer Peter Falk as a wacky grunt.
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18. HAVANA (1990)
Image Credit: Universal/Kobal/Shutterstock Directed by Sydney Pollack. Written by Judith Rascoe and David Rayfiel. Starring Robert Redford, Lena Olin, Alan Arkin, Raul Julia, Tomas Milian, Tony Plana, Richard Farnsworth, Mark Rydell.
“Havana” recycles many of the same elements from “Casablanca,” telling a story of passionate romance set against the backdrop of a war-torn, exotic locale. Robert Redford stars as an American gambler who finds himself in 1950’s Cuba during Castro’s takeover, where he quickly falls in love with a revolutionary’s wife (Lena Olin). Alan Arkin costars as a feisty casino owner, while Raul Julia turns up as Olin’s husband. Pollack tries to turn this premise into an epic, but there’s barely enough interesting elements to sustain its two-and-a-half hour runtime, although many parts are strong. Dave Grusin earned an Oscar nomination for his evocative score.
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17. THE INTERPRETER (2005)
Image Credit: Phil Bray/Working Title/Studio Canal/Kobal/Shutterstock Directed by Sydney Pollack. Screenplay by Charles Randolph, Scott Frank and Steven Zaillian, story by Martin Stellman and Brian Ward. Starring Nicole Kidman, Sean Penn, Catherine Keener, Jesper Christensen.
Pollack’s last film is a throwback to the paranoid political thrillers of the 1970s, including his own “Three Days of the Condor.” Though “The Interpreter” can’t hold a candle to those masterpieces, it’s still entertaining enough in its own right. Nicole Kidman stars as a South African interpreter who overhears an assassination plot at the United Nations. Sean Penn costars as the secret service agent assigned to protect her, and it’s a credit to the screenplay that these two don’t end up in bed together. Of special note: the movie was shot largely on location in the actual U.N. buildings, adding a heightened sense of reality to the proceedings.
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16. THIS PROPERTY IS CONDEMNED (1966)
Image Credit: Paramount/Seven Arts/Ray Stark/Kobal/Shutterstock Directed by Sydney Pollack. Screenplay by Francis Ford Coppola, Fred Coe and Edith Sommer, based on the one-act play by Tennessee Williams. Starring Natalie Wood, Robert Redford, Charles Bronson, Kate Reid, Mary Badham.
“This Property Is Condemned” was the first of seven movies Pollack made with Robert Redford, and he helped turn the blue-eyed hunk into a serious actor. Based on a play by Tennessee Williams, it casts him as a Depression-era railroad official who travels to Dodson, Mississippi, to shut down the town’s train station. While there, he falls in love with the beautiful girl (Natalie Wood) who lives at the boarding house he’s staying in. Yet her mother (Kate Reid) conspires to keep them apart. The once sultry story feels tame by today’s standards, but Redford and Wood are fantastic together. Francis Ford Coppola worked on the screenplay.
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15. THE SLENDER THREAD (1965)
Image Credit: Athene/Paramount/Kobal/REX/Shutterstock Directed by Sydney Pollack. Written by Shana Alexander, David Rayfiel, Stirling Silliphant. Starring Sidney Poitier, Anne Bancroft, Telly Savalas, Steven Hill, Ed Asner, Dabney Coleman.
Pollack made his feature debut with this tightly wound, self-important melodrama. Anne Bancroft stars as a woman who takes a lethal dose of sleeping pills, then calls a crisis hotline to talk with someone before she dies. She gets in touch with a student volunteer (Sidney Poitier) who tries to keep her on the line long enough to track her down and organize a rescue. The director creates as much suspense as he can with two people talking on a telephone, aided by capable performances from Bancroft and Poitier. Though a box office bomb, the film managed to snag Oscar bids for its black-and-white costumes and art direction.
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14. SABRINA (1995)
Image Credit: Moviestore Collection/REX/Shutterstock Directed by Sydney Pollack. Screenplay by Barbara Benedek and David Rayfiel, based on an earlier screenplay by Billy Wilder, Samuel A. Taylor and Ernest Lehman and a play by Taylor. Starring Harrison Ford, Julia Ormond, Greg Kinnear, Nancy Marchand, John Wood.
It’s possible that if Billy Wilder’s “Sabrina” had never existed, Pollack’s version would be better received. Yet Wilder’s 1954 classic looms large in our memories, making this 1995 remake feel like a pale imitation of the genuine artifact. Julia Ormond tries to fill Audrey Hepburn’s fashionable shoes as a chauffeur’s daughter who’s in love with the dashing playboy (Greg Kinnear) her father works for. But his business-minded older brother (Harrison Ford) has feelings of his own for the girl, and might be better suited for her. Though it can’t compete with the original, there’s enough style and romance to make for an entertaining night at the movies.
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13. BOBBY DEERFIELD (1977)
Image Credit: Columbia/Kobal/REX/Shutterstock Directed by Sydney Pollack. Written by Alvin Sargent, based on the novel by Erich Maria Remarque. Starring Al Pacino, Marthe Keller, Anny Duperey, Walter McGinn, Romolo Valli, Stephen Meldegg, Jaime Sanchez, Norm Neilson.
In “Bobby Deerfield,” Al Pacino plays a Formula One race car driver whose need for speed is curbed after a fiery crash kills a teammate and paralyzes a competitor. While visiting his fellow driver in the hospital, he falls in love with a young woman dying of cancer (Marthe Keller) who seems to become more beautiful the worse her disease gets. Dismissed as trash in its time, it’s since gained a well-deserved cult following. Cinematographer Henri Decae gorgeously captures the European countryside and thrilling auto races, while Dave Grusin’s score keeps things nice and weepy. Pacino earned a Golden Globe bid as Best Drama Actor for the film.
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12. THE ELECTRIC HORSEMAN (1979)
Image Credit: Moviestore/Shutterstock Directed by Sydney Pollack. Written by Paul Gaer and Robert Garland, story by Shelly Burton. Starring Robert Redford, Jane Fonda, Valerie Perrine, Willie Nelson, John Saxon, Wilford Brimley.
Pollack teams up with his favorite leading man and woman for a cheerfully old fashioned romantic comedy. “The Electric Horseman” casts Robert Redford as a washed-up rodeo star now wasting away in Vegas, earning a living by making public appearances with a prized stallion to sell cereal. When he finds out the evil advertisers are drugging the horse, he runs off to the desert with it. Jane Fonda costars as the plucky reporter who tracks him down, and the two strike up an improbable romance while evading the cops. There’s not much conflict in this amiable entertainment, which relies on Redford and Fonda’s star power for its impact.
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11. THE SCALPHUNTERS (1968)
Image Credit: United Artists/Kobal/REX/Shutterstock Directed by Sydney Pollack. Screenplay by William W. Norton, based on the novel by Ed Friend. Starring Burt Lancaster, Ossie Davis, Telly Savalas, Shelley Winters, Armando Silvestre, Nick Cravat, Dabney Coleman.
Burt Lancaster stars in this comedic western as a rugged fur trapper forced to trade some valuable pelts to a tribe of Kiowa Indians in exchange for an educated slave (Golden Globe-nominee Ossie Davis). Despite their differences, the two must pair up to recover the furs while evading a gang of scalphunters (led by Telly Savalas and Shelley Winters). Undoubtedly inspired by the Civil Rights Movement, Pollack adds in a message of racial harmony that sets this apart from other cowboy flicks of the era. But his approach is far from sanctimonious: rather, the film is pretty darn entertaining, thanks in large part to energetic performances.
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10. AMAZING GRACE (2018)
Image Credit: Amazing Grace LLC Directed by Sydney Pollack. Starring Aretha Franklin, James Cleveland, C. L. Franklin, Bernard Purdie, Chuck Rainey, Clara Ward, Mick Jagger, Sydney Pollack, Charlie Watts, Alexander Hamilton.
Pollack’s music documentary was besieged by production problems that kept it out of theaters for decades. Shot in 1972, it features Aretha Franklin recording her gospel album “Amazing Grace” at the New Bethel Baptist Church in Watts, Los Angeles. Originally planned to coincide with the album’s release, the film was shelved due to difficulties synching the footage with sound. It was taken over after Pollack’s death by producer Alan Elliott, who ran into legal trouble with Franklin. It finally hit screens after she passed away in 2018, and it was well worth the wait, because watching the soul legend perform with a live choir is truly electrifying.
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9. OUT OF AFRICA (1985)
Image Credit: Moviestore/REX/Shutterstock Directed by Sydney Pollack. Screenplay by Kurt Luedtke, based on the books “Out of Africa” by Isak Dinesen, “Isak Dinesen: The Life of a Story Teller” by Judith Thurman, and “Silence Will Speak” by Errol Trzebinski. Starring Robert Redford, Meryl Streep, Klaus Maria Brandauer.
Pollack hit the Oscar jackpot with this sweeping romantic epic, a sort of “Gone with the Wind” set in Africa. Loosely adapted from the autobiographical book by Isak Dinesen (aka Karen Blixen), it stars Meryl Streep as a Danish baroness who moves to Kenya with her husband (Klaus Maria Brandauer) in the early 20th century. While running a plantation, she falls in love with a dashing big game hunter (Robert Redford). Though its 161-minute runtime proceeds at the pace of a slug, the images are breathtaking, and Redford and Streep have a palpable chemistry. The film snagged seven Academy Awards, including Best Picture and Best Director for Pollack.
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8. THE YAKUZA (1975)
Image Credit: Moviestore/Shutterstock Directed by Sydney Pollack. Screenplay by Paul Schrader and Robert Towne, story by Leonard Schrader. Starring Robert Mitchum, Ken Takakura, Brian Keith, Herb Edelman, Richard Jordan, Keiko Kishi.
“The Yakuza” takes a B-level plot and executes it with A-level skill and craftsmanship. Robert Mitchum stars as an ex-G.I. who served in Japan during WWII, now working as a private eye in America. He returns to the country several years later to help an old friend (Brian Keith) rescue his kidnapped daughter from the infamous Japanese mafia. Ken Takakura costars as an old nemesis who helps Mitchum fulfill his mission. There’s enough kung fu action to satisfy martial arts fans, but there’s also a great deal of character development thanks to a cracker-jack script by three of Hollywood’s top writers (Paul Schrader, Robert Towne and Leonard Schrader).
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7. THE FIRM (1993)
Image Credit: Moviestore Collection/REX/Shutterstock Directed by Sydney Pollack. Written by David Rabe, Robert Towne, David Fayfiel, based on the novel by John Grisham. Starring Tom Cruise, Jeanne Tripplehorn, Gene Hackman, Ed Harris, Holly Hunter, Hal Holbrook, David Strathairn, Gary Busey.
If there were two things moviegoers could count on throughout the 1990s, they were Tom Cruise blockbusters and John Grisham adaptations. “The Firm,” therefore, gave ticket buyers a nifty two-for-one deal. This long, labyrinthine film centers on a young attorney (Cruise) who discovers there’s a dark side to the law firm he’s just joined. Pollack makes great use celebrity type-casting to create colorful characters in just a handful of scenes. Holly Hunter earned a Supporting Actress Oscar nomination for playing the chain-smoking, perm-wearing secretary to a private detective (Gary Busey) who helps the lawyer bring the company down.
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6. ABSENCE OF MALICE (1981)
Image Credit: Columbia/Mirage/Kobal/REX/Shutterstock Directed by Sydney Pollack. Written by Kurt Luedtke. Starring Paul Newman, Sally Field, Bob Balaban, Melinda Dillon, Luther Adler, Wilford Brimley.
“Absence of Malice” makes very little logical sense, but it sure is a lot of fun. It all starts when an intrepid reporter (Sally Field) gets some juicy information from an FBI investigator (Bob Balaban) about the disappearance of a union leader at the hands of a reclusive liquor wholesaler (Paul Newman). She runs with the story, only to be told by the accused man that it’s all lies. The two team up to find the truth, falling in love in the process. Questions of journalistic ethics aside, these two are great together, as is Melinda Dillon as Newman’s longtime friend. The film earned Oscar nominations for Newman, Dillon and Kurt Luedtke’s screenplay.
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5. JEREMIAH JOHNSON (1972)
Image Credit: Moviestore Collection/REX/Shutterstock Directed by Sydney Pollack. Screenplay by Edward Anhalt and John Milius, based on the books ‘Mountain Man’ by Vardis Fisher and ‘Crow Killer’ by Raymond W. Thorp and Robert Bunker. Starring Robert Redford, Will Geer, Allyn Ann McLerie, Stefan Gierasch, Charles Tyner, Delle Bolton.
Pollack’s epic western casts Robert Redford as a real life mountain man with legendary escapades. In the mid-1800s, ex-soldier Jeremiah Johnson spurns society to lead a solitary life in the Colorado Rockies. After a harsh winter, he gets some much-needed survival advice from a grizzled fur trapper named “Bear Claw” (Will Geer). Johnson soon sets up a home, adopting a young boy whose family was slaughtered and taking an Indian chief’s daughter for his bride. But a request by the U.S. Calvary could destroy everything he’s built. Shot on location in Utah, the film features some truly breathtaking images that make up for its slow pacing.
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4. THE WAY WE WERE (1973)
Image Credit: Columbia/Kobal/REX/Shutterstock Directed by Sydney Pollack. Written by Arthur Laurents. Starring Barbra Streisand, Robert Redford, Bradford Dillman, Viveca Lindfors, Herb Edelman, Murray Hamilton, Patrick O’Neal, Lois Chiles.
“The Way We Were” is a first class weepy, an unabashedly sentimental love story with two of Hollywood’s most charismatic stars. It centers on the politically-motivated Katie (Best Actress nominee Barbra Streisand) and the conservative Hubbell (Robert Redford) who fall in love when they meet at college in the late 1930s. Throughout the decades, their differences threaten to tear them apart, culminating in their breakup during the McCarthy era when Hubbell, a successful screenwriter, refuses to give up his career to do the right thing. Don’t forget the tissues when you watch this one! An Oscar winner for its melodic score and original title song.
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3. THREE DAYS OF THE CONDOR (1975)
Image Credit: Paramount/Kobal/REX/Shutterstock Directed by Sydney Pollack. Screenplay by Lorenzo Semple, Jr. and David Rayfiel, based on the novel ‘Six Days of the Condor’ by James Grady. Starring Robert Redford, Faye Dunaway, Cliff Robertson, Max von Sydow, John Houseman.
Released shortly after the Watergate scandal, “Three Days of the Condor” perfectly taps into the sense of paranoia permeating throughout the country at that time. Robert Redford stars as a meek CIA agent who returns to his office with lunch to find his coworkers murdered. It’s up to him to find the killers before they can knock him off too. Faye Dunaway costars as Redford’s love interest, while Max von Sydow steals the show as the mysterious murderer hunting him down. There’s not a wasted moment in the two hour runtime, and Pollock does an expert job of keeping the tension tightly wound from start to finish. An Oscar nominee for its film editing.
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2. THEY SHOOT HORSES, DON’T THEY? (1969)
Image Credit: Snap Stills/REX/Shutterstock Directed by Sydney Pollack. Screenplay by Robert E. Thompson and James Poe, based on the novel by Horace McCoy. Starring Jane Fonda, Michael Sarrazin, Susannah York, Gig Young, Bonnie Bedelia, Red Buttons, Michael Conrad, Bruce Dern.
This bleak, allegorical period drama propelled Pollack from B-list journeyman to A-list auteur. Set in Depression-era Los Angeles, “They Shoot Horses, Don’t They?” centers on a disparate group of strangers participating in a grueling all-night dance marathon, desperately trying to win the large cash prize. Jane Fonda headlines the ensemble cast as a suicidal contestant. The film earned nine Oscar nominations, including Best Director and Best Actress, winning for Gig Young’s supporting performance as the emcee who pushes the participants for his own gain. (It hold the record for the most bids earned by a movie that did not compete in Best Picture.)
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1. TOOTSIE (1982)
Image Credit: Columbia/Kobal/REX/Shutterstock Directed by Sydney Pollack. Screenplay by Larry Gelbart and Murray Schisgal, story by Gelbart and Don McGuire. Starring Dustin Hoffman, Jessica Lange, Teri Garr, Dabney Coleman, Charles Durning, Bill Murray, Sydney Pollack, George Gaynes, Geena Davis.
“Tootsie” finds Pollack in full command of his talent, perfectly blending comedy, romance, satire and pathos. The premise is so silly as to almost be disastrous: out of work actor Michael Dorsey (Dustin Hoffman) dresses in drag to get a job on a daytime soap, and his alter ego, Dorothy Michaels, becomes a national sensation. Yet it works thanks to a smart script (co-written by “M*A*S*H” creator Larry Gelbart) and strong performances by a rich ensemble, including Best Supporting Actress winner Jessica Lange as Michael’s costar/love interest and Pollack as his agent. The film earned nine additional Academy Award nominations, including Best Picture, Best Director, Best Actor and Best Original Screenplay.
