He appeared in "Iron Man 2" (2010) as Senator Stern and reprised the role in "" (2014). He appeared in an uncredited cameo as a health inspector in "The Dictator" (2012). He starred as himself representing Fox Mulder, alongside Téa Leoni as Dana Scully in "The X-Files" season 7 spoof episode "Hollywood A.D." In February 2010, Shandling was staying at the same Waipio Valley hotel that Conan O'Brien checked in to after his departure from The Tonight Show and spent the entire vacation together, Shandling helping to rehabilitate O'Brien. In January 2016, Shandling appeared on "Comedians in Cars Getting Coffee" with Jerry Seinfeld. Shandling never married and had no children. He revealed little about his personal life. He shared an apartment with his fiancée Linda Doucett from 1987 until 1994; on "The Larry Sanders Show", Doucett portrayed Darlene, Hank Kingsley's doting assistant. Shandling was a Buddhist who meditated, played a lot of basketball and boxed four times per week. Shandling owned a boxing gym, TSB 44 (Tough Strong Bold No. 44). in Santa Monica, California,  On February 4, 2019, Shandling's estate bestowed $15.2 million to benefit medical research at the David Geffen School of Medicine at UCLA. His gift will establish and endow the Garry Shandling Endocrine Surgery Research Fund, the Garry Shandling Infectious Diseases Innovation Fund and the Garry Shandling Pancreatic Diseases Fund. The remainder of the bequest will establish the Garry Shandling Medical Research Fund, which will operate under the direction of the medical school's dean. In his honor, UCLA also has named the Garry Shandling Learning Studio, a multipurpose space located in Geffen Hall, the school's medical education building. In 1994, when Shandling and his partner Linda Doucett ended their relationship, Shandling had her dismissed from "The Larry Sanders Show". Doucett filed a lawsuit against Shandling and Brad Grey's production company, Brillstein Entertainment Partners, for sexual harassment and wrongful termination. The case was settled out of court in 1997 for $1 million. In October 2017, television writer Janis Hirsch, who wrote for "It's Garry Shandling's Show", alleged that another actor put his genitals on her shoulder in front of Shandling while in his office and did so with impunity.