Rappaport is the son of Floyd A. Rappaport, a Detroit-born entertainment lawyer of Jewish descent who represented celebrities including Irwin Allen, Peter Lawford, and Steve McQueen. Rappaport graduated from the University of Southern California where he worked in real estate part-time. After school, he worked for Merrill Lynch Realty, Fred Sands Estates, and Stan Herman, Stephen Shapiro and Associates before co-founding the Westside Estate Agency in 1999 with Stephen Shapiro. In 2006, the agency added a Malibu office and booked more than $1 billion in sales with co-founders Rappaport and Shapiro ranked as the top two agents in Los Angeles County, according to the Los Angeles Times. As of 2015, WEA has over 100 full-time agents with offices in Beverly Hills, Malibu and Miami with over $3 billion in annual sales.
Rappaport has represented such personalities as Ellen DeGeneres, Ryan Seacrest,Tom Ford, Warren Beatty and Annette Bening, Tom Brady and Gisele Bundchen, Sean Parker, Sean Combs, Dr. Dre, Larry Ellison, who Rappaport represented on a buying spree that included 30 Malibu properties valued at more than $600 million.
In 2012, Rappaport founded Ora.tv, an online digital network distributed through Hulu, along with Carlos Slim and Larry King. Ora has offices in Los Angeles, New York City and Mexico City. Rappaport is also the executive producer of "London Fields", a feature film currently in post-production, starring Amber Heard, Billy Bob Thornton and Johnny Depp. The film is based on the New York Times Bestseller, London Fields, which was written by Martin Amis.
Rappaport was married to Juliette MacArthur, daughter of actor James MacArthur and granddaughter of actress Helen Hayes; they have three children. Rappaport is currently engaged to Canadian model, Sarah Mutch He owns a 6-acre Malibu estate valued at $100M that features the longest private pool in the State of California Prior to residing in Malibu, Rappaport sold his own home in Beverly Hills to Tom Cruise for $32.5M
On September 21, 2016, in New York City, Rappaport, along with Martin Scorsese, received The Friar's Club Icon Award, at a black-tie charity event hosted by Ryan Seacrest and Leonardo DiCaprio at Cipriani Wall Street. The Icon Award is the legendary club's highest honor and pays tribute to individuals whose accomplishments transcend their given industry by positively influencing culture. The award has been previously bestowed upon Douglas Fairbanks, Cary Grant, Frank Sinatra, Tom Cruise, Robert DeNiro, Tony Bennett and Carlos Slim.
In August 2016, Rappaport was named by Los Angeles Business Journal as one of the 500 Most Influential People In Los Angeles.