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Gwyneth Paltrow’s 10 Greatest Hits

Celebrate the 50th birthday of the actress-entrepreneur by watching her best movies

spinner image Gwyneth Paltrow attends The 2019 Met Gala Celebrating Camp: Notes on Fashion at Metropolitan Museum of Art on May 06, 2019 in New York City.
WireImage / Getty Images

Gwyneth Paltrow does not miss acting “at all,” she told Sunday Today in July 2021. OK for her, but we miss Paltrow, who hasn’t appeared on the big screen in a feature film since Avengers: Endgame in 2019.

With hits such as Emma and Sliding Doors, she could have been a contender for rom-com queen and America’s (and Britain’s) sweetheart status, but the Oscar-winning A-lister had an admirable “one for them, one for me” ethic as she alternated commercial fare with more challenging films such as Two Lovers and Sylvia.

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Since 2008, Paltrow has been immersed primarily in the universes of Marvel movies and Goop, her $250 million lifestyle brand. Paltrow turns 50 on Sept. 27, an ideal occasion to look back on 10 of her most indelible films and performances.

10. Se7en (1995)

The role: Tracy Mills

David Fincher’s bleak procedural pairs world-weary Detective Lieutenant Somerset (Morgan Freeman) with a new partner, David Mills (Brad Pitt). Paltrow is heartbreaking as David’s wife, who is struggling to settle in to life in the big, brutal city and can barely put on a brave face.

Indelible Gwyneth scene: Meeting Somerset in a diner, Tracy lets her facade crumble as she confides in him how much she hates the city and that she is pregnant. 

Watch it: Se7en, on Prime Video and Apple TV

9. Sylvia (2003)

The role: Sylvia Plath

Paltrow intensely embodies Sylvia Plath, who lived in the shadow of her celebrated husband, Ted Hughes (Daniel Craig), and only got her due after her works were published posthumously following her tragic suicide. Writing is hard to pull off credibly on-screen, but Paltrow makes you feel it when the words won’t come.

Indelible Gwyneth’s mom scene: We must pay homage to the magnificent Blythe Danner, Paltrow’s real-life mother, who gives a perfectly calibrated performance in the scene in which Sylvia’s mom tells Ted about one of Sylvia’s previous suicide attempts, saying: “Do you know that we found her right where you’re standing? Some people want to be found. Sylvia didn’t.” 

Watch it: Sylvia, on Prime Video and Apple TV

8. Two Lovers (2008)

The role: Michelle Rausch

Paltrow’s most memorable characters carry their baggage with varying degrees of functionality. Michelle is the new neighbor of Leonard (Joaquin Phoenix), the son of a dry-cleaning business owner who looks to sell out to another dry cleaner, and whose daughter might be a perfect match for Leonard. Michelle, on the other hand, is a married man’s mistress and uses drugs. You can see why Leonard is torn.

Indelible Gwyneth scene: While clubbing with Leonard, Michelle breaks down when her lover cancels on meeting her later. “He keeps telling me he’s going to leave them. … I never asked him to do that, and now I can’t think of anything else.” 

Watch it: Two Lovers, on Prime Video and Apple TV

7. Proof (2005)

The role: Catherine

“It’s been a pretty weird couple of years” for Paltrow’s Catherine, a brilliant student who dropped out of school to care for her late father (Anthony Hopkins), a brilliant mathematician who had descended into “instability.” Her estranged sister (Hope Davis) fears that Catherine, who lives as a depressive loner, may have inherited more than their father’s genius. Paltrow excels at playing flawed characters who live at the top of their intelligence.

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Indelible Gwyneth scene: “Not on the program,” Catherine interrupts her father’s packed memorial service. “I never knew he had this many friends,” she remarks. “Where have you all been for the past five years?” And then things get uncomfortable.

Watch it: Proof, on Prime Video and Apple TV

6. Hard Eight (1996)

The role: Clementine

Paul Thomas Anderson’s first feature is character actor heaven: Philip Baker Hall as Sydney, an “old-timer” in Reno by way of Atlantic City; John C. Reilly as John, his naive protégé; Samuel L. Jackson as the wild card; and Paltrow as Clementine, a cocktail waitress with whom John falls in love. She finds hard-bitten shadings to the hooker-with-a-heart-of-gold trope.

Indelible Gwyneth scene: Sidney discovers that Clementine hooks on the side, and she attempts to explain: “It’s so much different than what you think.” 

Watch it: Hard Eight, on Prime Video and Apple TV

5. Sliding Doors (1998)

The role: Helen

Paltrow plays not so much a double role as parallel lives: one in which she makes her subway train and arrives home to catch her boyfriend having sex with a former flame, and the other in which she does not.

Indelible Gwyneth scene: Helen goes on a “cheer-up date,” with all the requisite charming and witty banter one expects from a traditional romantic comedy. This one goes to some very dark places. 

Watch it: Sliding Doors, on Prime Video and Apple TV

4. Emma (1996)

The role: Emma Woodhouse

As Jane Austen’s heroine who appoints herself matchmaker and meddler in other people’s lives, Paltrow is at her most charming and winsome in this period adaptation of Clueless (just kidding!). This was the first film in which Paltrow adopted an English accent so spot-on that when she hosted Saturday Night Live three years later (and having since done Sliding Doors and Shakespeare in Love), she self-deprecatingly tried to pass herself off as a true Brit.

Indelible Gwyneth scene: Things get very arch-ery between Emma and her own (unexpressed) true love, Mr. Knightly (Jeremy Northam). She: “The most incomprehensible thing in the world to a man is a woman who rejects his offer of marriage.” He: “I do not comprehend it because it is madness.” 

Watch it: Emma, on Prime Video, Apple TV and HBO Max

3. The Talented Mr. Ripley (1999)

The role: Marge Duval

To Tom Ripley (Matt Damon), the life of wastrel golden boy Dickie Greenleaf (Jude Law) is aspirational, even if he has to kill him to get it, along with his ravishing and sophisticated girlfriend, Marge.

Indelible Gwyneth scene: Tom Ripley has conned one and all (and killed those he couldn’t). But when Marge finds the missing Dickie’s rings in Tom’s apartment, she knows something’s up, and she doesn’t believe a single thing a cornered Tom tries to tell her.

Watch it: The Talented Mr. Ripley, on Prime Video and Apple TV

2. The Royal Tenenbaums (2001)

The role: Margot Tenenbaum

Paltrow does this very affecting thing in Wes Anderson’s Salinger-adjacent saga about a family of child prodigies whose auspicious beginnings have been erased by “two decades of betrayal, failure and disaster.” She draws audiences in while her alienated character keeps family and loved ones at a distance. This includes her estranged father (Gene Hackman), who makes a point of introducing her as “my adopted daughter,” and her doting neurologist husband (Bill Murray).

Indelible Gwyneth scene: She has a special bond with her brother Richie (Luke Wilson), with whom she is reunited after he returns home upon the (fake) news that their father is dying. She emerges from a bus and, in ethereal slow motion, moves toward him with a haunting, enigmatic unblinking gaze that contains multitudes. The use of Nico’s otherworldly cover of Jackson Browne’s “These Days” could be the greatest needle-drop ever.

Watch it: The Royal Tenenbaums, on Hulu and Apple TV

1. Shakespeare in Love (1998)

The role: Viola De Lesseps

Of the eight films Paltrow made for Miramax, this was the Miramax-iest, right down to Harvey Weinstein’s controversially unprecedented Oscar campaign. The royally entertaining costume comedy won eight Academy Awards, including best picture and best actress for Paltrow, never more radiant, as Viola, an aspiring actress in an era when only male actors played female roles. She becomes a muse to a besotted William Shakespeare (Joseph Fiennes), but is their love to be or not to be?

Indelible Gwyneth scene: Viola takes the stage undisguised to the shock and astonishment of the audience, but to the ultimate approval of the queen (Judi Dench, an Oscar winner despite her scant eight minutes of screen time), who knows something of a woman in a man’s profession.

Watch it: Shakespeare in Love, on Prime Video, Apple TV and HBO Max

Donald Liebenson has written on film and entertainment for AARP, the Chicago Tribune, Chicago Sun-Times, Los Angeles Times, Vanity Fair and Entertainment Weekly.

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