'Everything about Diane was creativity personified,' said Francis Ford Coppola, the director of The Godfather trilogy, on hearing news of Diane Keaton’s death in 2025. Keaton had played Kay Adams Corleone in the films, one of several defining roles in a career that spanned more than five decades, across acting, directing, and writing. Her performances in Annie Hall, which earned her an Academy Award, Reds, Father of the Bride, and Something's Gotta Give established her as one of the defining screen presences of American cinema. Off screen, her oversized tailoring, hats, and menswear-inspired silhouettes cemented her status as a style icon, while her New York Times bestselling books California Romantica (2007) and The House that Pinterest Built (2017) extended her influence into architecture, interiors, and design.
This summer, the Diane Keaton Collection, a four-part auction series organised by Bonhams in partnership with The Fine Art Group, unfolds across New York and Los Angeles throughout June. Comprising more than 550 lots, the sales assemble the artefacts of Keaton’s life, from iconic wardrobe pieces and film memorabilia to the books, artworks, and domestic objects that populated her homes. Here, we highlight eight standout lots that offer insight into the people she loved, the films she made, the homes she built, the styles she cultivated, and the objects she chose to live with.
David Wojnarowicz’s Untitled (Buffalos) (1988-89). Estimate: US $25,000-35,000
Diane Keaton’s collection extended beyond fashion and film memorabilia to artworks displayed throughout her home, a 1926 Spanish-style house in Beverly Hills designed by Wallace Neff. A photograph by David Wojnarowicz appeared in the master bedroom alongside Western furniture and graduated Bauer pottery, reflecting the eclectic sensibility that shaped her interiors.
Created between 1988 and 1989, Untitled (Buffalos) followed a visit by Wojnarowicz to the Smithsonian National Museum of American History, where he encountered a diorama depicting Plains bison driven over cliffs. Having recently been diagnosed with AIDS, Wojnarowicz used the scene as an allegory for the government’s response to the epidemic. The falling buffalo became a symbol of abandonment and collective loss, themes that recurred throughout his work as he confronted homophobia, censorship and mortality. A lifelong admirer of California and the American West, Keaton also collected landscapes by Maynard Dixon and Ed Mell. Her photography book collection is also represented in the sale, with first editions by William Eggleston and Annie Leibovitz, among others.
Two framed mixed media collages by Diane Keaton. Estimate: US$1,000-1,500
Keaton’s interest in collage dates back to childhood. In her memoir Then Again, she recalled visiting the 1961 ‘Art of Assemblage’ exhibition at the Museum of Modern Art with her family and becoming captivated by the boxes of Joseph Cornell. ‘As soon as we got home, I decided to collage my entire bedroom wall,’ she wrote. The fascination was encouraged by her mother, Dorothy Hall, who filled 85 journals with scrapbook entries, photographs and collaged pages. Keaton carried the practice into adulthood, spending evenings making collages while trying to establish herself as an actor in New York and appearing in Broadway productions, including Hair. ‘I did a lot of collages. I couldn’t stop myself,’ she said in 2022. ‘I was really playing around with fantasies all the time.’
An original Annie Hall script. Estimate: $2,000-$4,000
An original mimeographed script for Annie Hall appears in the auction, bound in a red cover and inscribed ‘UNTITLED FILM SCRIPT / 4/15/76’, alongside two loose pages marked ‘NEW ENDING’. The 133-page document captures an earlier stage in the development of a film that would become one of the defining works of 1970s American cinema. Released in 1977, Annie Hall was the fourth collaboration between Diane Keaton and Woody Allen, earning four Academy Awards, including Best Picture, Best Director, Best Original Screenplay and Best Actress for Keaton.
The film also crystallised an aesthetic she would carry long beyond the screen: ties, oversized tailoring, hats and menswear reworked into something unmistakably her own. Allen developed the character with Keaton specifically in mind, drawing loosely on aspects of her personality and their earlier relationship. Even the title combined her childhood nickname, ‘Annie’, with her surname, Hall. Recalling the experience in her memoir, Then Again, Keaton wrote: ‘Filming Annie Hall was effortless… no one had any serious expectations.’ Allen encouraged her to ‘wear what you want to wear’, helping create a wardrobe that would become one of cinema’s most enduring style references.
A souvenir programme from the original Broadway production of Play It Again, Sam. Estimate: US$200-300
Before Annie Hall and long before her status as a Hollywood fixture, Diane Keaton starred as Linda Christie in the original 1969 Broadway production of Play It Again, Sam. Included in the sale is a souvenir programme from the production, together with a publicity photograph from the 1972 film adaptation, in which Keaton reprised the role opposite Woody Allen and Tony Roberts. The production ran for 453 performances at the Broadhurst Theatre and earned Keaton a Tony Award nomination for Best Featured Actress in a Play. It was during auditions for Play It Again, Sam that Keaton first met Allen, with their professional collaboration quickly developing into a romantic relationship. Play It Again, Sam was the first film Allen made with Keaton. The pair went on to collaborate on eight films between 1971 and 1993, including Annie Hall, Sleeper and Manhattan.
A pair of Louis Vuitton Star Trail ankle boots. Estimate: US $800-$1,200
A pair of black glazed calf leather Star Trail ankle boots by Louis Vuitton, offered in their original box and marked size 41, accompanied Diane Keaton to some of her most high-profile appearances over the past decade. She wore the chunky lace-up boots while accepting the AFI Life Achievement Award in 2017, styling them with a black turtleneck, belted silhouette, textured white jacket and her trademark wide-brimmed hat. Keaton later described the evening to The Hollywood Reporter as ‘the wedding [she] never had and the retirement party [she] never wanted’. During the ceremony, Al Pacino told his longtime collaborator: ‘You’re a great artist. I love you forever.’ The same pair reappeared at the premiere of Poms in Los Angeles in 2019, the Ralph Lauren show during New York Fashion Week in 2023, and numerous other engagements.
A Baron Hollywood’s Hat Maker black felt bowler hat with black ribbon. Estimate US$400-US$600
Few accessories are as closely associated with Diane Keaton as the black bowler hat. This example, by Baron Hats, was worn repeatedly throughout her life and career and belongs to a category of object that has become inseparable from her public image. The connection dates back to Annie Hall, where Keaton’s adoption of menswear-inspired tailoring and bowler hats helped establish one of cinema’s most enduring style signatures. In an interview with Vogue, Keaton said she owns around 40 hats, naming a plain black Baron bowler as her favourite: ‘I’ve had it for so long. It’s good – it’s dependable.’ Elsewhere, she described hats as ‘the final touch to a great outfit’. In her 2014 memoir, Let's Just Say It Wasn't Pretty, she wrote: ‘My hair is my hat. And my hat is my hair.’
A handwritten letter and inscribed sheet music for All I Have to Do Is Dream from Al Pacino. Estimate: US$300-$500
A handwritten note from Al Pacino and sheet music for ‘All I Have to Do Is Dream’, inscribed ‘To Di / Love AL’, sit among Diane Keaton’s personal papers. The accompanying letter reads: ‘Diane. Andy, me and Don went to a restaurant in Mondello. I will call you with the name of the joint. Sit tight. Be right. Don’t fight. Love Al, Your friend.’ Keaton and Pacino met while filming The Godfather and maintained an on-and-off romantic relationship into the 1980s. Keaton later described him as ‘the most entertaining man’ with ‘the most beautiful face’. Writing in Deadline following her death, Pacino said: ‘She lived without limits, and everything she touched carried her unmistakable energy,’ adding that she was ‘unstoppable, resilient, and above all, deeply human.’
Ed Ruscha signed book. Estimate: US$200-$300
Keaton’s sale includes several artist books by Ed Ruscha, among them a signed edition of Twentysix Gasoline Stations, first published in 1963. The publication comprises black-and-white photographs of petrol stations along the route between Los Angeles and Oklahoma City, with captions noting each location. The first stop was Bob’s Service in Los Angeles; the last, a Fina station in Groom, Texas. The lot also includes Nine Swimming Pools and Guacamole Airlines, alongside Sol LeWitt’s Modular Drawings. Keaton and Ruscha were romantically involved for a period, although little was made public about their relationship and both largely kept it out of view, unlike her more widely documented relationships with Al Pacino and Warren Beatty.