Hollywood

Expecting his first child, Jon Hamm joins long list of ‘old’ Hollywood dads

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…

Expecting his first child, Jon Hamm joins long list of ‘old’ Hollywood dads

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.

Westfeldt is a year older than Hamm, while Osceola is 17 years his junior. Of course, Hamm isn’t the first male celebrity to be an “old dad.” It’s a longstanding Hollywood tradition — a cliche even.

What Happened

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.

Advertisement
  • 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.

  • 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.

  • Then there is Steve Martin, now 80, who became a first-time father in 2012 at age 67 with his writer wife, Anne Stringfield.

Key Details

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.

  • Hugh Grant also became a first-time father in 2012 when he was 51, and has since gone on to have five children with two different women.

  • In 1992, at age 55, the star of “Bonnie and Clyde,” “Shampoo” and “Reds” married actor Annette Bening, then 34.

  • 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.

Why It Matters

Together, they quickly had four children.

  • Now 89, Beatty dated Natalie Wood, Joan Collins, Leslie Caron, Carly Simon, Julie Christie, Diane Keaton and Madonna, to name just a few.

What Reports Say

Coverage of the story so far points to:

  • Continued reporting by The Mercury News as more details emerge

Advertisement
Hollywood Expecting His First 2026 Updates

More in Hollywood

View all →