May-December celebrity couples Next Gallery 1 / 25 "The Fly" actor Jeff Goldblum is engaged to actress/contortionist Emilie Livingson, who is 30 his junior. 2 / 25 Clive Rose Supermodel Heidi Klum and Italian businessman Flavio Briatore have 23 years separating them. They dated briefly and have a daughter together. 3 / 25 Frazer Harrison "Beaches" actress Barbara Hershey dated "Lost" actor Naveen Andrews, 21 years her junior, for 12 years. 4 / 25 Scott Wintrow Actress Evan Rachel Wood is 19 years younger than former fiance Marilyn Manson. 5 / 25 Pascal Le Segretain Ivana Trump is 24 years older than ex-husband Rossano Rubicondi, whom she divorced in 2008 after seven months of marriage. 6 / 25 Larry Busacca Musician Billy Joel and TV personality Katie Lee had 32 years between them before they split in 2009 after 5 years of marriage. 7 / 25 Andreas Rentz Singer Celine Dion is 26 years younger than her husband and manager, Rene Angelil. 8 / 25 Imeh Akpanudosen Mogul Rupert Murdoch is 38 years older than his ex-wife, Wendi Deng Murdoch. 9 / 25 Charley Gallay Hugh Hefner is 60 years older than his wife Crystal. 10 / 25 Jamie McCarthy Actor James Woods is engaged to Kristen Bauguess, 46 years his junior. 11 / 25 Ben A. Pruchnie "The Green Mile" actor Doug Hutchison made headlines when he married teen singer Courtney Stodden, 35 years his junior. The pair have since divorced. 12 / 25 Dimitrios Kambouris Actor Hugh Jackman is 13 years younger than his actress wife Deborra-Lee Furness. 13 / 25 Stuart C. Wilson Singer Rod Stewart has been married to model Penny Lancaster, 18 years his junior, since 2007. 14 / 25 Kevin Winter Actor Dick Van Dyke is 46 years older than his wife Arlene Silver. 15 / 25 Frederick M. Brown Actor Lorenzo Lamas is 29 years older than his fiancee Shawna Craig. 16 / 25 Pascal Le Segretain Actor Jason Statham is 16 years older than his model/actress girlfriend, Rosie Huntington-Whiteley. 17 / 25 Pascal Le Segretain "Frasier" actor Kelsey Grammer (is 25 years older than his wife, Kayte Walsh. 18 / 25 Rob Kim Rocker Gregg Allman is 40 years older than his former fiancee, Shannon Williams. 19 / 25 Michael Buckner "Baywatch" actor David Hasselhoff is 27 years older than longtime girlfriend Hayley Roberts. 20 / 25 Brad Barket "30 Rock" actor Alec Baldwin is 25 years older than his wife, yoga instructor Hilaria. 21 / 25 Anthony Harvey "Snatch" director Guy Ritchie is 13 years older than his wife, model Jacqui Ainsley. 22 / 25 AP Actress Amber Tamblyn is married to Atlanta native and comedian David Cross, who is 19 years her senior. 23 / 25 AP Vivica A. Fox was engaged to Atlanta club promoter Omar "Slimm" White. She's 19 years older. 24 / 25 AP Bruce Willis and Emma Herning: He's 24 years older (and she's only eight years older than Willis' oldest daughter, actress Rumer). 25 / 25 Fred Dufour/Getty Images Harrison Ford and Calista Flockhart married in 2010. He's 68 and she's 46.