20 Best Sydney Pollack Movies: The Versatile Craftsman of American Film

Sydney Pollack was an American film director, producer, and actor who worked in the film industry for over five decades.

He is widely regarded as one of the most talented and versatile filmmakers of his generation, known for his ability to work across genres and his keen eye for storytelling and character development.

Pollack’s films often explored themes of identity, relationships, and the human condition, and he had a particular knack for bringing out nuanced and powerful performances from his actors.

He worked with some of the biggest stars in Hollywood, including Robert Redford, Meryl Streep, Dustin Hoffman, and Tom Cruise, and his films were often critically acclaimed and commercially successful.

In this article, we will take a look at some of the best Sydney Pollack films, including his most iconic works and some hidden gems.

Best Sydney Pollack Movies

We will explore the themes and techniques that made his films so memorable, and examine the impact he had on the film industry as a whole.

Whether you are a longtime fan of Pollack’s work or new to his films, there is much to discover and appreciate in his rich and varied filmography.

1. Tootsie (1982)

“Tootsie” is a 1982 comedy film directed by Sydney Pollack and starring Dustin Hoffman, who also served as a producer on the film.

The movie follows the story of Michael Dorsey (Hoffman), an out-of-work actor who decides to pose as a woman in order to get a part on a soap opera.

Under the guise of “Dorothy Michaels,” Michael becomes a sensation on the show, but finds himself increasingly drawn into the personal lives of his co-stars.

He also begins to develop feelings for his co-star, Julie (Jessica Lange), who believes him to be a woman.

“Tootsie” is widely regarded as one of the greatest comedies of all time, thanks to its sharp writing, strong performances, and insightful commentary on gender roles and identity.

The film earned ten Academy Award nominations and won Best Supporting Actress for Jessica Lange, as well as Best Original Screenplay.

Dustin Hoffman’s performance as Michael/Dorothy is widely regarded as one of the best of his career, and the film has become a beloved classic among audiences.

Its themes of self-discovery, acceptance, and the power of love and friendship continue to resonate with viewers today.

2. Out of Africa (1985)

“Out of Africa” is a romantic drama film released in 1985, directed by Sydney Pollack and starring Meryl Streep and Robert Redford.

The movie is based on the memoirs of Danish author Karen Blixen, who wrote under the pen name Isak Dinesen, and tells the story of her life in Kenya during the early 20th century.

The film follows Blixen’s journey as she marries a Swedish baron and moves to Kenya to run a coffee plantation.

Over time, she falls in love with a big-game hunter named Denys Finch Hatton, played by Redford, and the two begin a passionate and tumultuous relationship.

“Out of Africa” is notable for its sweeping cinematography, lush score, and nuanced performances from its leads.

The film won seven Academy Awards, including Best Picture, Best Director, and Best Adapted Screenplay. It’s considered one of the greatest romantic dramas of all time, and has been praised for its exploration of themes such as love, loss, and the complexities of colonialism.

Overall, “Out of Africa” is a beautifully crafted film that transports viewers to a bygone era in Africa. It’s highly recommended for fans of epic romance, period dramas, and classic Hollywood filmmaking.

3. The Swimmer (1968)

The Swimmer is a drama film that was released in 1968. The movie was directed by Frank Perry and written by Eleanor Perry, based on a short story by John Cheever.

The film stars Burt Lancaster in one of his most memorable roles, as a man named Ned Merrill who decides to swim his way home through the pools of his affluent neighbors.

The movie follows Merrill as he makes his way through the various pools of his community, encountering old friends and acquaintances along the way.

Through his interactions with these characters, it becomes clear that Merrill is not the man he appears to be and that his idyllic life is beginning to unravel.

The Swimmer is known for its surreal and dreamlike quality, with the swimming pools serving as a metaphor for Merrill’s descent into madness.

The film also explores themes of isolation, privilege, and the disillusionment of the American Dream.

Despite its critical acclaim, The Swimmer was not a commercial success upon its initial release. However, it has since become a cult classic among film enthusiasts and is widely regarded as one of Burt Lancaster’s finest performances.

The film’s unique blend of surrealism and social commentary has made it a favorite among fans of independent and art-house cinema.

4. Castle Keep (1969)

“Castle Keep” is a 1969 war film directed by Sydney Pollack and starring Burt Lancaster, Peter Falk, and Patrick O’Neal. Set in 1944 during the Battle of the Bulge, the movie tells the story of a group of American soldiers who are tasked with defending a medieval castle in Belgium.

As the war rages on around them, the soldiers, led by the eccentric and cynical Major Falconer (Burt Lancaster), begin to lose their sense of purpose and become disillusioned with their mission.

Meanwhile, a group of German soldiers, led by the cultured and erudite Captain Beckman (Patrick O’Neal), plot an attack on the castle.

“Castle Keep” is notable for its unique blend of war film and surrealism. The movie features stunning cinematography and visual effects, as well as a haunting and memorable score by Michel Legrand.

The characters are complex and well-developed, and the film explores themes of morality, duty, and the futility of war.

Despite mixed reviews upon its release, “Castle Keep” has become a cult classic and is widely regarded as one of the most underrated war films of all time.

The movie’s combination of action, humor, and surrealism, as well as its powerful anti-war message, make it a must-watch for fans of the genre.

5. They Shoot Horses, Don’t They? (1969)

“They Shoot Horses, Don’t They?” is a drama film released in 1969, directed by Sydney Pollack and starring Jane Fonda, Michael Sarrazin, and Gig Young.

The film is based on a novel of the same name by Horace McCoy and is set during the Great Depression. It tells the story of a group of desperate people who enter a dance marathon in order to win a cash prize.

The film explores the dark side of American society during the Depression era, including the exploitation of the poor and the desperation of those struggling to survive.

It also touches on themes such as the human condition, the lengths people will go to for survival, and the destructive nature of competition.

“They Shoot Horses, Don’t They?” is known for its strong performances, particularly by Jane Fonda, who was nominated for an Academy Award for her role.

The film was also nominated for nine other Oscars, including Best Picture, Best Director, and Best Supporting Actor for Gig Young, who won the award.

Overall, “They Shoot Horses, Don’t They?” is a powerful and thought-provoking film that offers a bleak look at American society during a difficult time in history.

It is a must-watch for fans of classic cinema and those interested in exploring the human condition.

6. The Way We Were (1973)

“The Way We Were” is a 1973 romantic drama film directed by Sydney Pollack and starring Barbra Streisand and Robert Redford.

The film tells the story of Katie Morosky (Streisand), a politically active college student, and Hubbell Gardiner (Redford), a carefree writer and former college athlete, who fall in love during their time at college in the 1930s.

As they graduate and move on with their lives, their political and personal differences strain their relationship, leading to a series of breakups and reunions over the years. T

he film explores themes of love, loss, and compromise, as Katie and Hubbell struggle to reconcile their differences and find a way to be together.

“The Way We Were” was a critical and commercial success, earning four Academy Award nominations and winning two, including Best Original Song for the film’s title track, sung by Streisand.

The film’s central love story has become a classic of romantic cinema, and the chemistry between Streisand and Redford is often cited as a highlight of the film.

In addition to its memorable performances, “The Way We Were” is notable for its depiction of political and social issues of the time, including McCarthyism and the Hollywood Blacklist.

Pollack’s deft handling of these sensitive topics adds depth and complexity to the film’s central love story, making it a compelling and resonant portrait of a tumultuous era.

7. The Yakuza (1974)

“The Yakuza” is a 1974 neo-noir action film directed by Sydney Pollack and written by Paul Schrader and Robert Towne.

The film stars Robert Mitchum, Ken Takakura, and Brian Keith, and tells the story of a former soldier who returns to Japan to help a friend repay a debt to the Yakuza, the Japanese criminal underworld.

The film is notable for its exploration of the cultural divide between the Western and Japanese worlds, as well as its examination of the complex codes of honor and loyalty that govern the Yakuza.

The action scenes are tense and well-executed, and the film’s themes of redemption, sacrifice, and the power of friendship give it an emotional depth that sets it apart from other crime dramas.

“The Yakuza” was not a commercial success upon its release in 1974, but it has since gained a cult following and is regarded as one of the best films of its genre.

The performances by Mitchum and Takakura are particularly strong, and the film’s moody cinematography and evocative score help to create a haunting atmosphere that lingers long after the credits roll.

8. Three Days of the Condor (1975)

“Three Days of the Condor” is a political thriller film released in 1975, directed by Sydney Pollack and starring Robert Redford, Faye Dunaway, and Max von Sydow.

The movie is based on the novel “Six Days of the Condor” by James Grady and tells the story of a CIA analyst named Joe Turner, played by Redford, who discovers a sinister plot within the agency.

After returning from lunch, Turner finds that all of his colleagues have been killed. Fearing for his own life, he goes on the run and begins to investigate the conspiracy that led to the murders.

Along the way, he meets a photographer named Kathy, played by Dunaway, who helps him uncover the truth.

“Three Days of the Condor” is a tense and suspenseful film that explores themes such as government corruption, surveillance, and the ethics of intelligence gathering.

The movie features a strong performance by Redford as the beleaguered protagonist, as well as notable turns by Dunaway and von Sydow as a ruthless hitman.

The film has become a classic of the political thriller genre and is highly recommended for fans of suspenseful dramas and conspiracy thrillers. It’s also a fascinating time capsule of the mid-1970s, capturing the paranoia and uncertainty of the era in which it was made.

9. Jeremiah Johnson (1972)

Jeremiah Johnson is a western film that was released in 1972. The movie was directed by Sydney Pollack and written by John Milius and Edward Anhalt, based on the story of the real-life mountain man John “Liver-Eating” Johnson. The film stars Robert Redford in the lead role, alongside Will Geer, Stefan Gierasch, and Allyn Ann McLerie.

The movie follows the story of Jeremiah Johnson, a former soldier who seeks to escape civilization and live a solitary life as a mountain man in the American West.

Johnson faces numerous challenges in the wilderness, including conflicts with Native American tribes, harsh weather conditions, and encounters with dangerous animals.

The film is known for its stunning cinematography, which captures the natural beauty of the American West. The movie also features a memorable musical score by composer John Rubinstein.

Jeremiah Johnson was a critical and commercial success upon its release, with many praising Redford’s performance and the film’s stunning visuals. The movie has since become a cult classic among fans of westerns and outdoor adventure films.

Its portrayal of a man seeking to escape the trappings of civilization and live a self-sufficient life in nature has resonated with audiences for decades.

10. The Slender Thread (1965)

“The Slender Thread” is a 1965 drama film directed by Sydney Pollack and starring Sidney Poitier and Anne Bancroft.

The movie follows a college student named Alan Newell (Sidney Poitier) who volunteers to answer the phone at a Seattle crisis center.

One night, he receives a call from a distraught woman named Inga Dyson (Anne Bancroft), who has taken an overdose of sleeping pills and needs help.

As the night wears on, Alan tries to keep Inga on the phone and find her location while also contacting the police and trying to keep her alive.

The film uses flashbacks to show Inga’s life and the reasons why she has reached this point of desperation.

“The Slender Thread” is notable for its tense and suspenseful atmosphere and its exploration of the human psyche.

The movie highlights the importance of mental health and the need for people to reach out and seek help when they are struggling. It also delves into the themes of loneliness, communication, and the fragility of life.

The film was praised for its performances by Poitier and Bancroft, as well as for its cinematography and score. “The Slender Thread” is a powerful and thought-provoking movie that still resonates with audiences today.

11. This Property Is Condemned (1966)

“This Property Is Condemned” is a drama film released in 1966, directed by Sydney Pollack and starring Natalie Wood and Robert Redford.

The film is based on a play by Tennessee Williams and is set in a small town in Mississippi during the Great Depression.

It tells the story of a young girl named Alva (played by Wood) who struggles to survive in poverty and dreams of a better life.

The film explores themes such as poverty, family dysfunction, and the pursuit of happiness. It also touches on the theme of isolation and the struggle for connection in a world that can be cruel and indifferent.

“This Property Is Condemned” is known for its strong performances, particularly by Natalie Wood, who delivers a powerful and nuanced portrayal of Alva. Robert Redford also shines in his role as Owen, a drifter who becomes involved with Alva.

Overall, “This Property Is Condemned” is a compelling and emotionally charged film that offers a poignant look at life during the Depression era. It is a must-watch for fans of classic cinema and those interested in exploring themes of poverty, family, and the human condition.

12. The Scalphunters (1968)

“The Scalphunters” is a 1968 Western film directed by Sydney Pollack and starring Burt Lancaster, Ossie Davis, Telly Savalas, and Shelley Winters.

The film tells the story of a fur trapper named Joe Bass (Lancaster) who is attacked and robbed of his pelts by a group of Kiowa Indians.

In the aftermath of the attack, Bass finds himself caught between two groups of scavengers who are after the pelts: a band of outlaw white scalphunters led by Jim Howie (Savalas), and a group of escaped slaves led by Joseph Lee (Davis), who are looking to secure their freedom with the pelts as bargaining chips.

“The Scalphunters” is notable for its blend of action, comedy, and social commentary. The film explores themes of racism, slavery, and the exploitation of Native Americans, while also featuring fast-paced action scenes and witty banter between the characters.

The performances by Lancaster, Davis, and Savalas are particularly noteworthy, with each actor bringing depth and complexity to their respective roles.

Although “The Scalphunters” was not a major commercial success at the time of its release, it has since become a cult classic among fans of the Western genre.

The film’s sharp humor and poignant social commentary have ensured its enduring relevance and appeal, and it remains a testament to Pollack’s skill as a filmmaker.

13. Bobby Deerfield (1977)

“Bobby Deerfield” is a 1977 drama film directed by Sydney Pollack and starring Al Pacino in the title role.

The film tells the story of a successful race car driver who falls in love with a terminally ill woman named Lillian Morelli (Marthe Keller) while in Europe for a Grand Prix race.

The film explores themes of love, loss, and mortality, as Bobby and Lillian grapple with the reality of her illness and the impact it has on their relationship.

Pacino delivers a nuanced performance as the emotionally guarded Bobby, while Keller brings a quiet strength and vulnerability to her role as Lillian.

Despite its strong performances and striking visuals, “Bobby Deerfield” received mixed reviews upon its release and was not a commercial success.

However, the film has since gained a cult following and is appreciated by many for its sensitive portrayal of a love affair that transcends societal norms and defies death itself.

Overall, “Bobby Deerfield” is a poignant and thought-provoking drama that showcases the talents of its director and star, and explores universal themes that continue to resonate with audiences today.

14. The Electric Horseman (1979)

“The Electric Horseman” is a drama film released in 1979, directed by Sydney Pollack and starring Robert Redford and Jane Fonda.

The movie tells the story of a former rodeo champion named Sonny Steele, played by Redford, who has become disillusioned with the commercialization of the sport.

In an act of defiance, he steals a prize-winning horse and sets out on a journey across the country to set the animal free.

Along the way, Sonny is pursued by a team of corporate executives and a determined reporter, played by Fonda, who is looking for a scoop.

The film explores themes such as the nature of fame, the exploitation of animals, and the pursuit of personal freedom.

“The Electric Horseman” is a visually stunning film that showcases the beauty of the American West and features strong performances from its two leads.

The movie also features a memorable score by composer Dave Grusin, which captures the spirit of the film’s themes and setting.

Overall, “The Electric Horseman” is a heartfelt and entertaining film that offers a poignant commentary on the state of modern society.

It’s recommended for fans of Robert Redford, Jane Fonda, and Sydney Pollack, as well as for anyone who enjoys character-driven dramas with a strong sense of place.

15. Absence of Malice (1981)

Absence of Malice is a legal drama film that was released in 1981. The movie was directed by Sydney Pollack and written by Kurt Luedtke.

The film features a star-studded cast, including Paul Newman, Sally Field, Bob Balaban, and Wilford Brimley.

The movie follows the story of Michael Gallagher, a businessman whose life is turned upside down when he is implicated in a federal investigation.

When a reporter named Megan Carter publishes a story about the investigation, Gallagher’s reputation is damaged and he becomes the target of public scrutiny.

As he fights to clear his name, Gallagher becomes involved in a complicated web of political corruption and personal betrayal.

Absence of Malice is known for its intelligent screenplay and strong performances by its cast. The film explores themes of journalistic ethics, political corruption, and the power of the media.

It also offers a nuanced portrayal of the legal system and the impact that a high-profile investigation can have on the lives of those involved.

Upon its release, Absence of Malice was a critical and commercial success, earning several Academy Award nominations, including Best Actor for Paul Newman and Best Supporting Actress for Melinda Dillon.

The film’s themes and complex characters have continued to resonate with audiences, making it a classic of the legal drama genre.

16. Havana (I) (1990)

Havana is a romantic drama film that was released in 1990. The movie was directed by Sydney Pollack and written by Judith Rascoe and David Rayfiel. The film stars Robert Redford, Lena Olin, and Alan Arkin.

The movie takes place in Havana, Cuba, in the late 1950s, just before the revolution. Jack Weil (Redford) is an American gambler who travels to Havana to make his fortune.

He meets a beautiful woman named Bobby Duran (Olin), who is married to a revolutionary (Arkin).

Despite their differences, Jack and Bobby fall in love, and they must navigate the dangerous political climate of pre-revolutionary Cuba to be together.

Havana is known for its lush cinematography and romantic storyline. The film explores themes of love, politics, and personal sacrifice, and is notable for its historical accuracy in depicting the tumultuous events leading up to the Cuban Revolution.

The movie received mixed reviews upon its release, with some critics praising its performances and visuals, while others criticized its slow pace and lack of action.

Despite this, Havana has since become a cult classic, with many fans appreciating its unique blend of romance and political intrigue.

17. The Firm (1993)

“The Firm” is a legal thriller film released in 1993, directed by Sydney Pollack and starring Tom Cruise, Gene Hackman, and Holly Hunter.

The film is based on a novel by John Grisham and follows a young lawyer named Mitch McDeere (played by Cruise) who is recruited by a prestigious law firm in Memphis, only to discover that the firm is involved in illegal activities.

The film explores themes such as corruption, greed, and the struggle to maintain one’s integrity in the face of temptation. It also touches on the theme of power and the lengths people will go to in order to protect it.

“The Firm” is known for its strong performances, particularly by Tom Cruise, who delivers a compelling portrayal of Mitch McDeere. Gene Hackman and Holly Hunter also shine in their roles as senior partners at the law firm.

Overall, “The Firm” is a gripping and suspenseful film that offers a thrilling look at the world of law and corruption.

It is a must-watch for fans of legal dramas and those interested in exploring themes of power, integrity, and morality.

18. Sabrina (1995)

“Sabrina” is a 1995 romantic comedy-drama film directed by Sydney Pollack and starring Harrison Ford, Julia Ormond, and Greg Kinnear.

The film is a remake of the 1954 classic of the same name, which was directed by Billy Wilder and starred Audrey Hepburn and Humphrey Bogart.

The story follows Sabrina Fairchild (Ormond), the daughter of a chauffeur who has been in love with the wealthy playboy David Larrabee (Kinnear) her whole life.

When she returns from a trip to Paris as a sophisticated and confident woman, David begins to see her in a new light.

However, complications arise when David’s older brother, Linus (Ford), tries to sabotage the relationship in order to secure a business deal.

Pollack’s direction of “Sabrina” emphasizes the film’s romantic comedy elements while also adding a layer of drama to the story.

The film features beautiful cinematography and a memorable score by John Williams.

The performances by the three leads are strong, with Ormond providing a charming and relatable performance as the titular character, and Ford and Kinnear showcasing their comedic and dramatic chops as the Larrabee brothers.

Despite mixed critical reception, “Sabrina” was a box office success and has since become a beloved romantic comedy-drama, known for its delightful performances and classic storyline.

Pollack’s direction, along with the strong chemistry between the cast members, helped to make the film a memorable entry in the romantic comedy genre.

19. Random Hearts (1999)

“Random Hearts” is a 1999 romantic drama film directed by Sydney Pollack and starring Harrison Ford and Kristin Scott Thomas.

The film is based on the novel of the same name by Warren Adler and tells the story of two strangers who are brought together by a tragic plane crash that claimed the lives of their respective spouses.

Ford plays Dutch Van Den Broeck, a police sergeant investigating the crash who discovers that his wife was having an affair with one of the victims, while Thomas plays Kay Chandler, a congresswoman whose husband was also on the plane.

The two initially clash due to their different backgrounds and personalities, but eventually form a bond as they try to come to terms with their grief and the secrets that have been uncovered.

The film explores themes of love, loss, betrayal, and the ways in which unexpected events can bring people together. Both Ford and Thomas deliver strong performances, and the film’s pacing and cinematography effectively capture the emotional journey of the characters.

While “Random Hearts” received mixed reviews upon its release and was not a commercial success, it is a compelling drama that offers a nuanced portrayal of grief and the complexities of human relationships. It is a testament to Pollack’s skill as a director and the talents of its cast.

20. The Interpreter (2005)

“The Interpreter” is a political thriller film released in 2005, directed by Sydney Pollack and starring Nicole Kidman and Sean Penn.

The movie tells the story of Silvia Broome, an interpreter at the United Nations in New York City, who overhears a plot to assassinate the controversial president of the fictional African nation of Matobo.

As Silvia becomes more involved in the investigation, she discovers that her own life is in danger, and she turns to a Secret Service agent named Tobin Keller, played by Penn, for help.

Together, they uncover a web of conspiracy and betrayal that threatens to destabilize the international community.

“The Interpreter” is a tense and intelligent thriller that explores themes such as international politics, justice, and the power of language. The movie features strong performances from its two leads, as well as notable supporting turns from Catherine Keener and Jesper Christensen.

The film’s climax takes place in the hallowed halls of the United Nations, which adds an extra layer of intrigue and tension to the proceedings.

Overall, “The Interpreter” is a well-crafted thriller that offers a thought-provoking look at the complexities of global politics and the importance of communication. It’s highly recommended for fans of political thrillers and intelligent dramas.

3 Characteristics of Sydney Pollack Films

Sydney Pollack was a highly respected director and producer known for his versatility and ability to work across a wide range of genres. Here are three characteristics that are commonly found in his films:

Emphasis on character-driven narratives: Pollack’s films often explore complex characters and their relationships with one another.

He was known for his ability to coax strong performances from his actors and for his nuanced portrayals of human emotions and motivations. This focus on character development helped to create compelling and relatable stories that resonated with audiences.

Exploration of societal issues: Pollack’s films often tackled important societal issues, including politics, corruption, and the human condition.

He was known for his ability to handle weighty themes with sensitivity and insight, creating films that were both thought-provoking and entertaining.

Attention to detail: Pollack was a meticulous filmmaker who paid close attention to every aspect of his films, from the script to the cinematography to the music.

He was known for his ability to create immersive and believable worlds on screen, and for his attention to detail in everything from costume design to set decoration.

This level of craftsmanship helped to create films that were visually stunning and emotionally resonant.

3 Reasons Why You Should Watch Sydney Pollack Films

Sydney Pollack was a highly acclaimed director, producer, and actor who made a significant impact on Hollywood. Here are three reasons why you should watch Sydney Pollack films:

Strong Performances: Pollack had a talent for working with actors and bringing out their best performances.

He worked with some of the biggest names in Hollywood, including Robert Redford, Meryl Streep, Dustin Hoffman, and Tom Cruise, to name a few.

Pollack’s films often showcase powerful and nuanced performances that are both memorable and impactful.

Relevant Themes: Pollack’s films often explored relevant and thought-provoking themes that are still relevant today.

For example, his film “The Firm” examines corruption in the legal system, while “They Shoot Horses, Don’t They?” delves into the darker side of human nature and desperation. Pollack’s films often leave a lasting impression on viewers and offer insights into the human condition.

Diverse Body of Work: Pollack directed a diverse range of films, from romantic dramas like “Out of Africa” to suspenseful thrillers like “Three Days of the Condor.”

He also tackled a variety of genres, including Westerns, comedies, and war films. As a result, there is something for everyone in Pollack’s filmography, making him a versatile and well-respected filmmaker.

Best Sydney Pollack Films – Wrapping Up

In conclusion, Sydney Pollack was a talented director whose films covered a wide range of genres and themes, from romantic comedies to political thrillers to Westerns.

Some of his best films include “Out of Africa,” “Tootsie,” “The Way We Were,” “Three Days of the Condor,” and “They Shoot Horses, Don’t They?” Each of these films showcases Pollack’s skillful direction, nuanced storytelling, and ability to draw out memorable performances from his cast.

Pollack’s legacy as a filmmaker has had a lasting impact on the industry, inspiring generations of filmmakers to follow in his footsteps.

His films continue to be celebrated for their timeless themes, masterful storytelling, and unforgettable performances, cementing his place in cinematic history as one of the greats.