The Rat Pack (1998)

In the 1950s and 1960s, Frank Sinatra was the head of the infamous "Rat Pack". He, Sammy Davis Jr., Dean Martin, Peter Lawford, and Joey Bishop worked and played together. This film dramatizes their volatile relationships with one another and the Kennedys, Marilyn Monroe, mobster Sam Giancana, Judith Campbell Exner, and the FBI. Sinatra helps John F. Kennedy get elected in 1960 with a little help from Giancana. Lawford, married to a Kennedy, is an unhappy go-between. Davis is fighting racism and insecurity. Campbell is sleeping with both Giancana and JFK, who is also sleeping with Monroe.