Martha Raye, 34 years older than husband Mark Harris. She was 75, and he was 41 when they married on September 25, 1991. The marriage ended with her death on in 1994. This was her seventh marriage. Her shortest marriage lasted less than a year, and her longest lasted for 11 years.
The wedding–Ivana's fourth–was said to include 25 bridesmaids, a 12 foot-tall cake carved from chocolate by German pastry chefs and a 25-piece orchestra flown in from Paris.
Among the 300 guests were Ivana's ex-husband Donald Trump and his 37-year-old third wife, Melania; Ivana and Donald's three children; singer-songwriter Neil Sedaka; Janice Combs, mother of music mogul P. Diddy; actress Brigitte Neilsen, the ex-wife of Sylvester Stallone; David Koch, the seventh-richest man in the United States; Kathy and Rick Hilton, the parents of Paris; and sex expert Dr. Ruth Westheimer.
Ivana announced in December 2008 that she and her new husband were splitting up. "Rossano wants to live in Miami and work in Milan," Trump said. "But, I am a New Yorker and my family, friends and businesses are here. As the beautiful song says, `Que sera sera!'"
Barbara Hershey, 21 years older than Naveen Andrews. Living together in committed relationship as of 2006.
Mary Kay Letourneau Fualaau, 21 years older than husband Vili Fualaau. Teacher Mary Kay was convicted and served seven years in prison for "second-degree child rape" of her then 13-year-old student. She was released in 2004 and married Fualaau in May 2005. They have two daughters. She also has four children from her previous marriage.
Norma Shearer, 20 years older than her second husband, Sun Valley ski instructor Martin Arrouge, who she married in 1942 after being widowed in 1936 by her first husband, producer Irving Thalberg. Norma and Martin were married for 41 years until she died in 1983.
Elizabeth Taylor, 20 years older than husband Larry Fortensky. They married in October 1991 and divorced five years later.
María Félix, 20 years older than and Antoine Tzapoff. She was a Mexican diva, he is a French plastic artist. She died in 2002.
Francesca Annis, 18 years older than Ralph Fiennes. Fiennes had been married to "ER" star Alex Kingston at the time he met Francesca, while Annis had three children with photographer Patrick Wiseman. They met when she played his mother in a London stage production of Hamlet. They decided to separate after Ralph allegedly had an affair with a young singer in February 2006.
Dinah Shore, 20 years older than Burt Reynolds. Dinah was one of the most popular singers in the US in the 1940s and 1950s and eventually had her own TV show. She had a long relationship with Burt.
Ruth Gordon, 16 years older than husband Garson Kanin.
Estelle Parsons, 16 years older than husband Peter Zimroth. They adopted a son in 1983.
Demi Moore, 15 years older than her husband, Ashton Kutcher. They married in 2005. She has three daughters from her previous marriage.
Mariah Carey, 12 years older than husband, Nick Cannon. The singer married the actor in May 2008.
Susan Sarandon, 12 years older than her longtime partner, Tim Robbins. They have two children together. She announced in late 2009 that they had separated in the summer of 2009 after 23 years together. There were then rumors that she had a new boyfriend, Jonathan Bricklin, age 31, 32 years younger than her. She's an investor in Bricklin's Manhattan ping pong Bar. She denied the rumors.
Naomi Watts, 11 years older than Heath Ledger. Their relationship did not lead to marriage.
Lisa Loeb, 10 years older than Roey Hershkovitz. Lisa, 40, a singer and songwriter, and her husband, age 30, the music coordinator on “Late Night with Conan O'Brien”were married Saturday evening, January 31, 2009 at Brasserie 8 ½, a restaurant in New York City. Rabbi Andy Bachman officiated. Lisa had her own reality show on cable TV a few years earlier, called "Number One Single," in which she was looking for the right guy to marry.
Madonna, 10 years older than her husband, Guy Ritchie. They have a son together, Rocco, and also her daughter, Lola, from a previous relationship. And they adopted a young boy from Africa named David Banda. They divorced in January 2009.
Halle Berry, 9 years older than boyfriend Gabriel Aubrey. She met Aubry, 31, while shooting a Versace ad in November 2005. " The twice-divorced actress said in March 2007: "After my last relationship [with actor Michael Ealy] broke up I was feeling like, well, it wasn't that I didn't want to be in a relationship, it's just that I thought it would be okay to be on my own. But he was disarmingly sweet and caring and different. In the past I've been attracted to big personalities. Gabriel was shy. He hardly talked to me at first." But that just made him more appealing. "I had to work at this a little," she says. "It wasn't a slam dunk; it wasn't the guy just showering affection on me. It made it more interesting. We were equally matched – put it that way."
Sheryl Crow, 9 years older than Lance Armstrong. They were engaged but broke up before getting married.
Vanessa Redgrave, 9 years older than Timothy Dalton. The relationship did not lead to marriage.
Linda Evans, 8 years older than Yanni, who she dated for 9 years until they broke up.
Anne Hathaway, 8 years older than William Shakespeare. They married when she was 26 and he was 18.
Nancy Grace, 7 years older than Atlanta Investment banker David E. Linch, who news reports say is 41. She and Linch met in Mercer College many years ago and stayed in touch over the years. When she was much younger, Nancy lost her first fiance through violent crime. She went on to become a prosecutor and TV news show anchor as a victim's rights advocate. Nancy and David for married in April 2007 and Nancy gave birth to twins in late 2007. Their names are John and Lucy.
Yoko Ono, 7 years older than John Lennon. They were married and had one son, Sean. The marriage ended when John was murdered.
Eva Longoria, 7 years older than Tony Parker. They met in 2004 and have been an item since. Eva told People Magazine, "There's no way in the world I would rather be single." "I've said the only reason Tony and I are going to stay together forever is because we're too lazy to look for someone else." Their European wedding is set for July 7, 2007.
Lucille Ball, 6 years older than Desi Arnaz. They married in 1940 and divorced on May 4, 1960. They had two children, Lucie and Desi, Jr.
Janet Jackson, 6 years older than her long-term boyfriend Jermaine Dupri.
Tom Cruise, 6 years younger than his then-wife, Mimi Rogers.