It’s easy to see how Jon Hamm is following a similar path as Don Draper, the handsome but elusive 1960s advertising executive he played on “Man Men.” After splitting from his longtime female partner, who’s more or less his contemporary, Hamm, like Draper, has taken up with a much younger woman.

In Hamm’s case, he’s also now starting a family with his new partner, actor Anna Osceola, making him a first-time father at 55.

While Draper got kicked out of the house by Betty, the mother of his three children, and married his pretty young secretary, Hamm ended an 18-year relationship with actor, screenwriter and occasional collaborator Jennifer Westfeldt in 2015. Westfeldt is a year older than Hamm, while Osceola is 17 years his junior. She also had a small role in “Mad Men.” Hamm and Osceola married in 2023 — in a cliffside ceremony in Big Sur overlooking the Pacific Ocean.

Before it was reported this week that the “Your Friends & Neighbors” star and Osceola were expecting a baby, he told The Hollywood Reporter that he was looking forward to finally having children, as People reported. “It’s not lost on me that I’m (in my 50s),” he admitted. “I will be the old dad, but so it goes. It could be a good thing. We’ll see.”

SANTA MONICA, CALIFORNIA - MARCH 12: Anton Pacino, Olivia Pacino, Al Pacino and Julie Pacino at Aero Theatre on March 12, 2026 in Santa Monica, California. (Photo by Matei Horvath/Getty Images for UTOPIA) 

Of course, Hamm isn’t the first male celebrity to be an “old dad.” It’s a longstanding Hollywood tradition — a cliche even. There’s a long list of famous male celebrities who have welcomed babies with much-younger wives and girlfriends when they are in their 50s, 60s, 70s and even their 80s: Robert De Niro, Al Pacino, Bruce Willis, Mick Jagger, Alec Baldwin, Mel Gibson, Eddie Murphy and Richard Gere.

Hamm also belongs in a sub-set of this cliche: Male celebrities who become first-time fathers when they are 50 or older.

US actor and filmmaker Mel Gibson (C) and his children Lucia (L) and Lars attend a special screening of "Monster Summer" at the DGA Theater Complex in Los Angeles on September 24, 2024. (Photo by VALERIE MACON / AFP) (Photo by VALERIE MACON/AFP via Getty Images) 

George Clooney, once one of Hollywood’s most famous bachelors, became a first-time father at age 56 in 2017 when his wife Amal Clooney, then 39, gave birth to twins. After Justin Theroux split from 57-year-old Jennifer Aniston in 2018, the now-55-year-old actor married 32-year-old actor Nicole Brydon Bloom last year. Theroux became a first-time father to a son in April, with the couple announcing on Instagram: “He’s here. We are so in love.”

Then there is Steve Martin, now 80, who became a first-time father in 2012 at age 67 with his writer wife, Anne Stringfield. Hugh Grant also became a first-time father in 2012 when he was 51, and has gone on to have five children with two different women.

Perhaps the most famous case of a male celebrity who got started late in fatherhood, after making a name for himself as a bachelor who enjoyed the company of a variety of women, is Warren Beatty. Now 89, Beatty dated Natalie Wood, Joan Collins, Leslie Caron, Carly Simon, Julie Christie, Diane Keaton and Madonna, to name just a few. In 1992, at age 55, the star of “Bonnie and Clyde,” “Shampoo” and “Reds” married actor Annette Bening, then 34. Together, they quickly had four children.

As for Hamm, he opened up in a 2022 interview with Howard Stern about finally being ready to settle down, marry and have children after he met Osceola, as People reported.

“This is another place in my life that I feel very settled and comfortable,” Hamm said on Stern’s SiriusXM show. “I’m in a relationship right now and it’s comfortable.” He also said the relationship is “more meaningful and (has) opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness.”