By his early teens Sinatra had begun performing at local clubs. At the age of 19, he became the vocalist for
Sam Donahue's band. He also spent considerable time with
Duke Ellington, learning the music business. Sinatra spent most of his early career on the road. In 1965, he composed music for the film,
the Beach Girls and the Monster. By 1968, he had performed in 47 states and 30 countries, had appeared as a guest on several television shows including two episodes of
The Smothers Brothers Comedy Hour with his sister Nancy, hosted a 10-week summer replacement series for
The Dean Martin Show, had sung with his own band in
Las Vegas casinos, and had been the opening act for bigger names at other casinos. During that time, he gained a reputation for rigorous rehearsals and demanding high standards for his musicians. Sinatra appeared in the
Sammy Davis Jr. drama
A Man Called Adam in 1966. He also played a disturbed man who takes a stewardess hostage and later as officer Tom Boyd in three episodes of the television crime drama
Adam-12, the last episode of which was titled "Clinic on 18th Street" (originally broadcast on March 13, 1974). This episode was an edited television pilot for a
Mark VII Limited series that was not sold. His other acting credits included roles in
Aru heishi no kake (1970) with
Dale Robertson,
Code Name Zebra (1987) opposite
James Mitchum, and
Hollywood Homicide (2003) with
Harrison Ford and
Josh Hartnett. The United States
National Archives now houses a 15-minute song and monologue composed by Sinatra in 1976, "Over the Land". It evokes the memory of the U.S. flag and the nation's experiences with the flag since the
War of 1812. Starting in 1988, at his father's request, Sinatra placed his career on hold in order to act as his father's musical director and conductor. Poet/vocalist
Rod McKuen said: In 1989, Sinatra sang "Wedding Vows in Vegas" on the
Was (Not Was) album,
What Up, Dog?, and performed the song live with the band on
Late Night with David Letterman on March 23, 1989. During the 1997–1998 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.
James Darren accepted the part, after refusing three times because he found the idea of a vocalist playing a vocalist to be too "on the nose", but changed his mind when he read the script. Sinatra guest-starred in an episode of
Son of the Beach, in the episode "You Only Come Once" (2002), playing the villain Stink Finger, and he sang his own theme song for the character. He had a guest spot playing himself in an episode of
The Sopranos, "
The Happy Wanderer" (2000), in a role either mocking or acknowledging all the stories about his father's involvement with the mob – he lets
Paulie Walnuts refer to him as the "Chairboy of the Board". Sinatra appeared in the show
Family Guy, season 4, episode 19: "
Brian Sings and Swings", wherein he was introduced as the "Member of the Board". He performed several tunes during the show, accompanied by
Stewie and
Brian. During the ending credits, he sang the
Family Guy theme song. He also recorded a commentary for its DVD release. He returned in a 2008 episode, "
Tales of a Third Grade Nothing" (Season 7, Episode 6), wherein he sang with Brian again, with Stewie returning as a sideline investor supporting the duo. A third episode featuring Sinatra, "
Bookie of the Year" (Season 15, Episode 2), aired posthumously on October 2, 2016, and was dedicated to his memory. This was his final screen appearance. In 2006, Sinatra released the album
That Face!, including the songs "You'll Never Know" and the self-penned song "Spice". Sinatra made a brief cameo appearance in the series premiere episode of the 2010 CBS legal comedy-drama
The Defenders, as well as the show's series finale. On August 17, 2015, Sinatra sang "
The Star-Spangled Banner" at
Yankee Stadium. and sang the "
Theme from New York, New York" at the
2014 Belmont Stakes. Sinatra appeared with
Tierney Sutton on
Patrick Williams' 2015 CD
Home Suite Home, performing "I've Been Around." It is believed to be his last studio session. The recording earned a
Grammy Award nomination for
Best Large Jazz Ensemble Album. Sinatra's song "Black Night", written and sung by him, was used as the theme song to
Rick Alverson's feature film
Entertainment (2015), starring
Gregg Turkington and
John C. Reilly. ==Personal life==