By his early teens, Sinatra was performing at local clubs and venues.
At age 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.
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 standards for his musicians.

 Sinatra appeared in the Sammy Davis Jr. drama A Man Called Adam in 1966.
He also played a deputy district attorney, named Gino Bardi, on the television crime drama Adam-12, in the episode titled "Clinic on 18th Street" (originally broadcast on March 13, 1974).
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 National Archives now houses a 15-minute song and monologue composed by Sinatra in 1976, Over the Land.
It evokes the memory of the nation'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:
As the senior Sinatra outlived one by one all of his conductors and nearly every arranger, and began to grow frail himself, his son knew he needed someone that he trusted near him. [
Frank Jr.] was also savvy enough to know that performing was everything to his dad and the longer he kept that connection with his audience, the longer he would stay vital and alive.

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 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.
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 on 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 on 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." (
His sister, Nancy, also appeared as herself in a later Sopranos episode "Chasing It" (2007).

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 8, 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 appearance recorded.

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
By his early teens, Sinatra was performing at local clubs and venues. At age 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. 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 standards for his musicians.
 Sinatra appeared in the Sammy Davis Jr. drama A Man Called Adam in 1966. He also played a deputy district attorney, named Gino Bardi, on the television crime drama Adam-12, in the episode titled "Clinic on 18th Street" (originally broadcast on March 13, 1974). 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 National Archives now houses a 15-minute song and monologue composed by Sinatra in 1976, Over the Land. It evokes the memory of the nation'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:
As the senior Sinatra outlived one by one all of his conductors and nearly every arranger, and began to grow frail himself, his son knew he needed someone that he trusted near him. [Frank Jr.] was also savvy enough to know that performing was everything to his dad and the longer he kept that connection with his audience, the longer he would stay vital and alive.
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 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. 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 on 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 on 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." (His sister, Nancy, also appeared as herself in a later Sopranos episode "Chasing It" (2007).
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 8, 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 appearance recorded.
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 
Frank Sinatra Jr.