In a bizarre incident, Sinatra was kidnapped on December 8, 1963 at Harrah's Lake Tahoe and released two days later after his father paid out the US$240,000 ransom demanded by the kidnappers, who were later captured, prosecuted, convicted, and sentenced to long prison terms. Gladys Root represented one of the kidnappers. In order to communicate with the kidnappers via pay telephone as they demanded, his father carried a roll of dimes with him throughout this ordeal, which became a life-long habit. The kidnapping has been described in Act Three of the "Plan B" episode of the radio narrative show, This American Life by Barry Keenan, one of the kidnappers. The kidnapping is portrayed in the 2003 made-for-TV movie Stealing Sinatra, which is based on Barry Keenan's story.
At the time of trial, Keenan attempted to make it appear that Sinatra, Jr. himself was a willing conspirator in his own kidnapping, with the motive of attempting to get more attention from his busy father. This allegation didn't stand up in court, but still proved to be fodder for late-night TV jokes, with unsympathetic publicity aimed at the younger Sinatra. Frank, Jr.'s widely reported first words upon his release and return home were, "I'm sorry, Dad." Some speculated this was an admission of guilt. The media coverage, mostly negative in tone, could only have a detrimental effect on the younger Sinatra's fledgling career.
Frank Sinatra, Jr. has played at times in Las Vegas in the footsteps of his father, but this seemed to invite almost invariably negative comparisons. On seeing the act, Forbes Magazine editor Malcolm Forbes remarked, "Junior sure ain't Senior!," to which several readers wrote to ask if he would like his son Steve Forbes to be referred to in the same manner. Frank, Jr. appeared in the Sammy Davis, Jr. television drama A Man Called Adam in 1966 and hosted a summer replacement series while the popular The Dean Martin Show was on hiatus in 1968. Since both Davis and Martin were close friends of Frank, Sr., it further fueled the notion that Frank, Jr.'s career was built on nepotism.
In the later stages of his father's performing career, Frank Sinatra, Jr. became his father's musical director and conductor.
In 1989, Sinatra did a cameo vocal on the acclaimed Was (Not Was) album, "What Up, Dog?" on Chrysalis Records, singing "Wedding Vows In Vegas" with the band. He also appeared with WNW doing that song on Late Night With David Letterman on NBC the same year.
During the 1995/1996 television season, Sinatra was offered the role of Vic Fontaine on Star Trek: Deep Space Nine. Despite being a fan of the show and finding the role interesting, he turned it down, declaring that he only wanted to play an alien. (Star Trek: Deep Space Nine Companion)
He also had a guest spot playing himself on The Sopranos, in a role where it was unclear if he was mocking or acknowledging all the stories about his father's involvement with the mob, and where he lets the character Paulie Walnuts refer to him as the "Chairboy of the Board".
Sinatra appeared in a 2006 episode of Family Guy, "Brian Sings and Swings" (Season 4, Episode 19) where he was introduced as the "Member of The Board". He performs several tunes during the show, accompanied by Stewie and Brian. During the ending credits, he sings the Family Guy theme song. He also recorded a commentary for its DVD release.
On June 12, 2006, Sinatra was scheduled to appear as a guest on The Howard Stern Show but walked out moments before the interview took place because he refused to sign a mandatory guest release. Eye witnesses, including the show's producer Gary Dell'Abate claimed that Sinatra was already in a foul mood when he entered the studio offices, which culminated in a fit when Sinatra lashed out and broke a CD and other items against a wall. Sinatra's publicist then asked Dell'Abate to remove an article from the release which demanded the guest have their person searched; Dell'Abate tried to oblige, but Sinatra was already gone by the time he returned to the guest waiting room. Howard Stern, upon hearing this news, asked: "Doesn't he know he's Frank Sinatra, Junior?"
In 2006, Sinatra recorded a new album entitled "That Face" including songs like "You'll Never Know" and the self-penned song "Spice."
