Jean Smart And Richard Gilliland's Love Story, Crossword Puzzle Flirt And The Rose Garden Wedding
Jean Smart recently won an Emmy Award on September 14, 2026. The actress has been married to Richard Gilliland since 1987, and they have two children.
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Add BollywoodShaadis on GoogleJean Smart made Emmy history at the 78th Primetime Emmy Awards on September 14, 2026. The 74-year-old star won Outstanding Lead Actress in a Comedy Series for HBO Max's Hacks, playing legendary comic 'Deborah Vance.'
Jean’s win marks her eighth career Emmy, tying the all-time record with Julia Louis-Dreyfus and Cloris Leachman. It is also her fifth victory for Hacks, making her the first performer ever to win for every season of a single series. Amid her latest win at the Emmy Awards, Jean’s personal life has now grabbed attention, including her relationship with Richard Gilliland.
Jean Smart and Richard Gilliland tied the knot a year after they first met
Jean Smart and Richard Gilliland's love story lasted more than three decades and began in the most Hollywood way possible. They met in 1986 on the set of the CBS sitcom Designing Women, where Smart was a series regular playing 'Charlene Frazier-Stillfield.'
Gilliland had been cast for a guest arc as 'J.D. Shackelford,' the boyfriend of Annie Potts' character 'Mary Jo.' Smart has told the story many times that she literally met him while he was kissing someone else on camera. In fact, he had previously dated her co-star Delta Burke and had worked with the rest of the cast before, making Smart the only one he didn't know.
Jean was instantly attracted to Richard’s smile and his quick, cheeky humor. She asked Burke to casually find out if he was married, and once she learned he wasn't, she found a way to get his attention. She invited him into her trailer to help her with crossword puzzles, a line that even Julia Louis-Dreyfus joked about later.
Richard invited Jean to see a play he was in, and she said she went 17 times. After just a few days, she told him she was only being nice because it was her week to take care of the guest star, but he didn't buy it.
The pair tied the knot in June 1987 in the rose garden of co-stars Dixie Carter and Hal Holbrook's home. A little over a year later, Smart realized she was pregnant while sitting in her dressing room in Charlene's tight corseted wedding dress. The writers wrote the pregnancy into the show. Their first son, Connor Douglas, was born in October 1989.
For many years, Gilliland stepped back from acting to raise their family so Smart could travel for work. The couple also loved working together when they could. They appeared together in theater and in the fifth season of 24, where Richard played ‘Captain Stan Cotter’ while Jean played ‘Martha Logan.’ In 2009, they adopted their second son, Forrest, from China.
Their marriage lasted 34 years until Gilliland's sudden death on March 18, 2021, at the age of 71, after a brief illness. Smart has often said she wouldn't have had her career without his support.
Richard Gilliland has pursued a successful career in the entertainment industry
Richard Gilliland was a well-known film, television, and stage actor born on January 23, 1950, in Fort Worth, Texas. He began his career in the 1970s after studying in Kansas, appearing in shows like Thirtysomething, The Waltons, and Little House on the Prairie before landing his most recognized guest role as 'J.D. Shackelford,' the boyfriend of 'Mary Jo Shively,' on the CBS sitcom Designing Women in 1986.
Richard went on to amass over 90 screen credits across four decades, including roles in Airplane II: The Sequel, The White Shadow, Operation Petticoat, Heartland, Party of Five, Dexter, Desperate Housewives, CSI, and 24. On stage, he was a respected theater actor in Los Angeles. He was also a part of films like Bug, Star Kid, and Breaking Up.
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