Steve Martin's ''Shopgirl'' inspires our countdown of the oldest actors most often paired with the youngest actresses
Claire Danes, Steve Martin, ...
Credit: Shopgirl: Sam Emerson

Steve? Woody? Jack? We rate Hollywood’s 10 top cradle robbers

Wait a minute. Is that Steve Martin romancing Claire Danes — an actress less than half his age — in Shopgirl? Well, that must be what passes for reality in Hollywood, the land where actors play sexually desirable characters well into their AARP years. The result is several decades of movies whose senior-and-ingenue couples can’t help but give off a Humbert-and-Lolita vibe.

Though extreme examples of on-screen cradle robbing may seem cringe-worthy, moviegoers continue to make May-December romances into hits. Clearly, older male stars— heroes like Sean Connery, Clint Eastwood, and Harrison Ford, and comfortably familiar comic charmers like Martin or Woody Allen — still know how to turn wishful thinking about the appeal of older males into a big-screen reality. At least Shopgirl addresses the age gap; most movies don’t even acknowledge the strangeness of a 20-to-30 year difference between the romantic leads. And, despite a Mrs. Robinson every now and then, actresses rarely get the same leeway. Just look at Uma Thurman, whose romance as an ancient 37-year-old with a 23-year-old beau is presented as a real shocker in the new movie Prime. Did we just hear the words ”double standard”?

In the following gallery, we look at the romantic roles of 10 veteran leading men. We chose five movies that paired each of them with much younger love interests (plus, to be fair, one role opposite an older actress). Then we added the age gaps and came up with an unscientific, but nonetheless revealing, average. Read on as we count down to the old goat who got our highest age-gap rating. Then post your thoughts about the trend on our scribble board.

Image credit: Autumn In New York: Kobal Collection

Richard Gere

(born 1949)

Richard Gere has romanced a few much-younger costars

HIS PERSONA Suave, handsome leading man whose brooding exterior hides a volatile streak. His romantic partners try to breach his stoicism and unleash his passion.

HIS WOMEN Diane Lane, the wife whose infidelity drives him to violence in 2002’s Unfaithful (born 1965, 16 years younger)
Winona Ryder (pictured), the terminally ill young woman who tries to get aging playboy Gere to settle down in 2000’s Autumn in New York (born 1971, 22 years younger)
Bai Ling, his defense attorney in 1997’s Red Corner (born 1970, 21 years younger)
Julia Ormond, Guinevere to Gere’s Lancelot in 1995’s First Knight (born 1965, 16 years younger)
Julia Roberts, the streetwalker Cinderella who is wined and dined by a wealthy john (Gere) in 1990’s Pretty Woman (born 1967, 18 years younger)

THE EXCEPTION Susan Sarandon, his wife in 2004’s Shall We Dance (born 1946, 3 years older)

FUN FACT Gere is 12 years older than wife Carey Lowell and 17 years older than ex-wife Cindy Crawford (born 1961 and 1966, respectively).


Image credit: A Perfect Murder: Everett Collection

Michael Douglas

(born 1944)

Michael Douglas has romanced a few much-younger costars

HIS PERSONA Slick, privileged professional man with a sense of entitlement. To women, he appears to be a good provider, one with a taste for luxury.

HIS WOMEN Famke Janssen, his wife in 2001’s Don’t Say a Word (born 1964, 20 years younger)
Gwyneth Paltrow, an heiress who is married to bond trader Douglas, takes a lover (Viggo Mortensen, pictured at left) in 1998’s A Perfect Murder (born 1972, 28 years younger)
Demi Moore and Caroline Goodall, his ex-lover and his wife in 1994’s Disclosure (born 1962 and 1959, 18 and 15 years younger, respectively)
Sharon Stone, and Jeanne Tripplehorn, a murder suspect and a police psychiatrist, both of whom get freaky with the detective played by Douglas in 1992’s Basic Instinct (born 1958 and 1963, 14 and 19 years younger, respectively)
Kathleen Turner, estranged wife of acquisitive lawyer Douglas in 1989’s The War of the Roses (born 1954, 10 years younger)

THE EXCEPTION Candice Bergen, ex-wife to Douglas’ danger-seeking CIA agent in 2003’s The In-Laws (born 1946, 2 years younger)

FUN FACT Douglas is married to Catherine Zeta-Jones (born 1969, 25 years his junior).

AVERAGE AGE GAP 15.8 years

Image credit: As Good As It Gets: Everett Collection

Jack Nicholson

(born 1937)

Jack Nicholson has romanced a few much-younger costars

HIS PERSONA Confident, brash rebel whose arched eyebrows signify a not-too-secret devilish side. Of course, that wicked streak makes him seem like a fun guy to be around.

HIS WOMEN Amanda Peet and Diane Keaton, as his young fling and her mother, in 2003’s Something’s Gotta Give (born 1972 and 1946, 35 and 9 years younger, respectively)
Helen Hunt (pictured), the grateful waitress he wins over with a surprising act of generosity in 1997’s As Good as It Gets (born 1963, 26 years younger)
Jennifer Lopez, his partner-in-crime in 1996’s Blood & Wine (born 1969, 32 years younger)
Ellen Barkin, his dog-training client in 1992’s Man Trouble (born 1954, 17 years younger)
Cher, Susan Sarandon, and Michelle Pfeiffer, the amateur enchantresses who conjure up his demonic presence in 1987’s The Witches of Eastwick (born 1946, 1946, and 1958, 9 and 21 years younger, respectively)

THE EXCEPTION June Squibb, the wife of retiree Nicholson in 2002’s About Schmidt (born 1929, 8 years older)

FUN FACT From 1999 to 2002, Nicholson had an on-and-off relationship with Lara Flynn Boyle (born 1970, 33 years his junior.)

AVERAGE AGE GAP 16.7 years

Image credit: Scarface: Everett Collection

Al Pacino

(born 1940)

Al Pacino has romanced a few much-younger costars

HIS PERSONA A soulful, streetwise scrapper who’s a ticking time bomb

HIS WOMEN Elizabeth Berkley, a hooker impressed by a veteran pro football coach (Pacino) in 1999’s Any Given Sunday (born 1972, 32 years younger)
Penelope Ann Miller, a stripper girlfriend to Pacino’s gangster in 1993’s Carlito’s Way (born 1964, 24 years younger)
Ellen Barkin, the murder suspect pursued by Pacino, as a detective in 1989’s Sea of Love (born 1954, 14 years younger)
Nastassia Kinski, a Tory-turned-patriot inspired by his idealism and fighting spirit as a colonist in 1985’s Revolution (born 1961, 21 years younger)
Michelle Pfeiffer, the moll to drug kingpin Pacino in 1983’s Scarface (born 1958, 18 years younger)

THE EXCEPTION Dyan Cannon, the Broadway star seeking a career boost in a play he’s written in 1982’s Author! Author! (born 1937, 3 years older)

FUN FACT Scheduled to play Pacino’s student and love interest in the upcoming 88 Minutes is Alicia Witt (born 1975, 35 years his junior).

AVERAGE AGE GAP 17.7 years

Image credit: LA Story: The Kobal Collection

Steve Martin

(born 1945)

Steve Martin has romanced a few much-younger costars

HIS PERSONA He’s long since evolved from wild and crazy guys to playing urbane, tightly wound, often flustered guys. Despite his antics, his prematurely gray hair has always given him an appearance of paternal stability.

HIS WOMEN Claire Danes, the title sales clerk wooed by software tycoon Martin in 2005’s Shopgirl (born 1979, 34 years younger)
Helena Bonham Carter and Laura Dern, his dental patient and his assistant in 2001’s Novocaine (born 1966 and 1967, 21 and 22 years younger, respectively)
Heather Graham, the ambitious starlet seeking to beef up her role in the movie he’s directing in 1999’s Bowfinger (born 1970, 25 years younger)
Sarah Jessica Parker (pictured) and Victoria Tennant, the Southern California gals pursued by a wistful weatherman (Martin) in 1991’s L.A. Story (born 1965 and 1950, 20 and 5 years younger, respectively)
Daryl Hannah, the astronomer he charms via a more handsome surrogate in 1987’s Roxanne (born 1960, 15 years younger)

THE EXCEPTION Goldie Hawn, his wife in 1999’s The Out-of-Towners (born 1945, same age)

FUN FACT The female lead in Martin’s next movie, The Pink Panther, is Beyoncé (born 1981, 36 years his junior).

AVERAGE AGE GAP 17.8 years

Image credit: Six Days Seven Night: Everett Collection

Harrison Ford

(born 1942)

Harrison Ford has romanced a few much-younger costars

HIS PERSONA Earnest man of action, often somber, sometimes brash. Women find his competence and resourcefulness reassuring, but he also radiates the sense of a wounded inner child that arouses maternal feelings.

HIS WOMEN Michelle Pfeiffer, his haunted wife in 2000’s What Lies Beneath (born 1958, 16 years younger)
Kristin Scott Thomas, the bereaved Congresswoman who comforts a similarly bereaved cop, played by Ford, in 1999’s Random Hearts (born 1960, 18 years younger)
Anne Heche (pictured), the dizzy career gal stranded with a rough-edge pilot (Ford) in 1998’s Six Days, Seven Nights (born 1969, 27 years younger)
Julia Ormond, the chauffeur’s daughter wooed by Ford as an uptight tycoon in 1995’s Sabrina (born 1965, 23 years younger)
Alison Doody, the treacherous archaeologist who trysts with both Indiana Jones and his father in 1989’s Indiana Jones and the Last Crusade (born 1965, 23 years younger)

THE EXCEPTION Helen Mirren, his passive wife in 1985’s The Mosquito Coast (born 1945, 3 years younger)

FUN FACT Ford’s girlfriend is Calista Flockhart (born 1964, 22 years his junior).

AVERAGE AGE GAP 18.3 years

Image credit: Legal Eagle: Kobal Collection

Robert Redford

(born 1936)

Robert Redford has romanced a few much-younger costars

HIS PERSONA Diffident, reserved outdoorsman with enduring golden-boy looks. Women think of him both as a protector and as someone they can coax out of his shell.

HIS WOMEN Kristin Scott Thomas, the city gal who falls under rancher Redford’s spell in 1998’s The Horse Whisperer (born 1960, 24 years younger)
Michelle Pfeiffer, the rookie he mentors into a news anchor in 1996’s Up Close & Personal (born 1958, 22 years younger)
Demi Moore, the woman whose affections he tries to buy in 1993’s Indecent Proposal (born 1962, 26 years younger)
Lena Olin, the Ingrid Bergman to his Humphrey Bogart in 1990’s Havana (born 1955, 19 years younger)
Debra Winger and Daryl Hannah (pictured), the young lawyer and artist who compete for his affections in 1986’s Legal Eagles (born 1955 and 1960, 19 and 24 years younger, respectively)

THE EXCEPTION Jane Fonda, as the journalist who tracks down fugitive cowboy Redford in 1979’s The Electric Horseman (born 1937, 1 year younger)

FUN FACT Early on, Robin Wright Penn was up for the female lead in Up Close & Personal (born 1966, 30 years younger).

AVERAGE AGE GAP 19.3 years

Image credit: In the Line of Fire: Everett Collection

Clint Eastwood

(born 1930)

Clint Eastwood has romanced a few much-younger costars

HIS PERSONA The quietest of quiet types, he exudes mystery that women find intriguing. He retains even in his older years a muscular masculinity and sex appeal.

HIS WOMEN Wanda De Jesus, who hires sleuth Eastwood to find her sister’s killer in 2002’s Blood Work (born 1958, 28 years younger)
Laila Robins, his boss’ wife, with whom he’s having an affair, in 1999’s True Crime (born 1959, 29 years younger)
Meryl Streep, the bored housewife who has an affair with a well-traveled photographer (Eastwood) in 1995’s The Bridges of Madison County (born 1949, 19 years younger)
Rene Russo (pictured), a fellow Secret Service agent in 1993’s In the Line of Fire (born 1954, 24 years younger)
Patricia Clarkson, a TV newswoman reporting on the police work of Dirty Harry in 1988’s The Dead Pool (born 1959, 29 years younger)

THE EXCEPTION Shirley MacLaine, the firebrand rescued by cowboy Eastwood in 1970’s Two Mules for Sister Sara (born 1934, 4 years younger)

FUN FACT Since 1996, Eastwood has been married to the former Dina Ruiz (born 1965, 35 years his junior).

AVERAGE AGE GAP 22.2 years

Image credit: Entrapment: Everett Collection

Sean Connery

(born 1930)

Sean Connery has romanced a few much-younger costars

HIS PERSONA Rugged, gruff, wily, unflappable, macho hero. Even in his bald years, his absolute self-confidence and sense of adventure continue to endow him with sex appeal.

HIS WOMEN Catherine Zeta-Jones (pictured), his partner-in-crime in 1999’s Entrapment (born 1969, 39 years younger)
Julia Ormond, Queen Guinevere to Connery’s King Arthur in 1995’s First Knight (born 1965, 35 years younger)
Tia Carrere as a digital video whiz who helps a cop (Connery) solve a murder in 1993’s Rising Sun (born 1967, 37 years younger)
Lorraine Bracco, a research scientist who accompanies Connery, as a crusading doctor, on an Amazon rain forest adventure in 1992’s Medicine Man (born 1954, 24 years younger)
Kim Basinger, a Bond girl in 1983’s Never Say Never Again (born 1953, 23 years younger)

THE EXCEPTION Gena Rowlands, his wife in 1998’s Playing by Heart (born 1930, same age)

FUN FACT Connery was 59 when People magazine named him its ”Sexiest Man Alive” in 1989.

AVERAGE AGE GAP 26.3 years

Image credit: Manhattan: Everett Collection

Woody Allen

(born 1935)

Woody Allen has romanced a few much-younger costars

HIS PERSONA Nervous nebbish who attracts women with his wit. He’s often a teacher or mentor figure to women, who ultimately mature and outgrow him.

HIS WOMEN Téa Leoni, Debra Messing, and Tiffani Thiessen, movie folk in the orbit of a famous director (Allen) in 2002’s Hollywood Ending (born 1966, 1968, and 1974, 31, 33, and 39 years younger, respectively)
Julia Roberts, the married woman he seduces after learning her fantasies by eavesdropping on her therapist in 1996’s Everyone Says I Love You (born 1967, 32 years younger)
Helena Bonham Carter as his wife and Mira Sorvino as a prostitute he tries to lift from the gutter in 1995’s Mighty Aphrodite (born 1966 and 1967, 31 and 32 years younger, respectively)
Mia Farrow as his estranged wife and Juliette Lewis as his student in 1992’s Husbands and Wives (born 1945 and 1973, 10 and 38 years younger, respectively)
Mariel Hemingway (pictured), a high school student in 1979’s Manhattan (born 1961, 26 years younger)

THE EXCEPTION Louise Lasser, a political activist he tries to impress in 1971’s Bananas (born 1939, 4 years younger)

FUN FACT Allen has been married to Soon-Yi Previn (born 1970, 35 years younger) since 1997; it’s the longest to date of his three marriages.

AVERAGE AGE GAP 27.6 years

Hollywood Age Gap: Talk About It

The age difference in movie romances just keeps getting larger. Do you think it matters?

Hollywood’s cradle robbers: Talk about it

With Steve Martin romancing Claire Danes — who is 34 years younger — in Shopgirl, Hollywood continues to support the fantasies of older males who think their appeal may be never-ending. But now, with help from our guide to the on-screen romances of Hollywood’s top cradle robbers, it’s time for you to chime in. Are older men more credible as romantic leads than older women? Does it matter that men in their 60s are so often cast to romance women in their 30s? Is it okay that Uma Thurman is presented as an ancient 37-year-old because of her romance with a 23-year-old beau in Prime? Share your thoughts about Hollywood’s age gap here.

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