At 54 Sinatra posed for Playboy in the May 1995 issue and made appearances on TV shows to promote her album One More Time. The magazine appearance caused some controversy. On the talk show circuit, she said her father was proud of the photos. Those close to the Sinatras claimed that family members were upset with the nude photo spread. Sinatra told Jay Leno on a 1995 Tonight Show that her daughters gave their approval, but her mother said she should ask her father before committing to the project. Sinatra claims that when she told her father what Playboy would be paying her, he said, "Double it.
She and Lee Hazlewood embarked on a US tour playing the House of Blues, the Viper Room, the Whiskey-a-Go-Go, the now-defunct Mama Kin in Boston, the Trocadero in Philadelphia, and The Fillmore.
That year, Sundazed Records began reissuing Sinatra's Reprise albums with remastered sound, new liner notes and photos, and bonus tracks. She also updated her biography on her dad and published Frank Sinatra: An American Legend.
In 2003 she reunited with Hazlewood once more for the album Nancy & Lee 3. It was released only in Australia.
Taking her father's advice from when she began her recording career ("Own your own masters"), she owns or holds an interest in most of her material, including videos.
In 2004 she collaborated with former Los Angeles neighbour Morrissey to record a version of his song "Let Me Kiss You", which was featured on her autumn release Nancy Sinatra. The single — released the same day as Morrissey’s version — charted at #46 in the UK, providing Sinatra with her first hit for over 30 years. The follow-up single, "Burnin' Down the Spark", failed to chart. The album, originally titled To Nancy, with Love, featured rock performers such as Calexico, Sonic Youth, U2, Pulp's Jarvis Cocker, Steven Van Zandt, Jon Spencer, and Pete Yorn, who all cited Sinatra as an influence. Each artist crafted a song for Sinatra to sing on the album.
Two years later EMI released The Essential Nancy Sinatra – a UK-only greatest-hits compilation featuring the previously unreleased track, "Machine Gun Kelly". The collection was picked by Sinatra and spans her 40-year career. The record was Sinatra's first to make the UK album charts (#73) in 30 years.
Sinatra appeared, as herself, on one of the final episodes (Chasing It) of the HBO mob drama The Sopranos. Her brother, Frank Jr., had previously appeared in the 2000 episode The Happy Wanderer.
Sinatra recorded a public service announcement for Deejay Ra's 'Hip-Hop Literacy' campaign, encouraging reading of Tarantino screenplays and related books.
September 2009 saw the release of Sinatra's digital-only album Cherry Smiles: The Rare Singles, featuring previously unreleased tracks and songs only available on 45.
Sinatra now hosts a weekly show on Sirius Satellite Radio, Siriusly Sinatra, where she shares her personal insights about her father
Trivia
Mother of A.J. Lambert and photographer Amanda Lambert (born March 17, 1976).
Phil Silvers wrote the lyrics to the Jimmy Van Heusen song "Nancy (With the Laughing Face)" for Nancy Sinatra in honor of her 4th birthday
Began her singing career in 1965 after she divorced Tommy Sands.
Had 24 Billboard hits. Her most famous songs are 'These Boots Are Made for Walkin',' 'How Does That Grab You, Darlin'?' 'You Only Live Twice,' 'Sugar Town,' 'Lightning's Girl,' 'Some Velvet Morning,' 'Lady Bird,' 'Somethin' Stupid,' 'Love Eyes,' 'Did You Ever?' and 'The Highway Song,' as well as cult songs 'Bang Bang,' 'Kinky Love,' 'Hook and Ladder' and 'Flowers in the Rain.' Sinatra also has two Adult Contemporary chart favorites, 'Happy,' and the hard-to-find 'How Are Things in California?
Released a disco single in 1976 called Kinky Love, on Private Stock. The song's suggestive lyrics made the song unplayable to radio waves, and was only heard every so often in underground of the late 70's. It first gained resurrection when in the early 1990's, The Pail Saints covered the song for an album, but really rose attention when Nancy herself included on a 1998 compilation of rare and unreleased tracks called "Sheet Music." Today, the song is widely recognized as a cult hit of Sinatra's (being the talk of different places on the Internet), and original copies of the single [Private Stock 075] is a sought-after
collectors item; rarely ever seen at all. Some copies sell for over $1,000 dollars.
Her first hit record, "These Boots Are Made for Walkin'", became popular partly due to the prominent bass guitar riff played throughout the song. That riff was played by Chuck Berghofer, with Carol Kaye on rhythm guitar. Both are of the legendary Wrecking Crew.
Received a star on the Hollywood Walk of Fame [May 11, 2006].
Performed "Somethin' Stupid" with brother Frank Sinatra Jr. on "The Smothers Brothers Comedy Hour" (1967). Nancy and father Frank Sinatrahad just had a number 1 hit with the song in the US and the UK, the only father-daughter duet ever to top the charts. [April 30, 1967]
She was awarded a Star on the Hollywood Walk of Fame for Recording at 7000 Hollywood Boulevard in Hollywood, California.