Although Frank Sinatra died almost 20 years ago, his image is larger than life and his stature and mystique have endured beyond his death. Ol’ Blue Eyes would have turned 100 this December, and publishers are marking the occasion by releasing books that celebrate his legacy, several of them abundantly illustrated with never-before-seen photographs.

The biggest Sinatra book of the season—coming in at 992 pages—is James Kaplan’s Sinatra: The Chairman (Doubleday, Oct.), the second volume of his monumental biography and the follow-up to Frank: The Voice, released by Doubleday in 2010. PW’s starred review called The Voice an “enthralling tale of an American icon that serves as an introduction of Ol’ Blue Eyes to a new generation.” With a first print run of 100,000, Kaplan’s newest volume picks up Sinatra’s story on the day after he wins his Academy Award in 1954, portraying him candidly as the cruel and kind, romantic and petty perfectionist he could be.

Poet and critic David Lehman celebrates the Sinatra centennial in a series of impressionistic fan’s notes of the singer and movie star in Sinatra’s Century: One Hundred Notes on the Man and His World (Harper, Oct.). Lehman uses remembrances of his own encounters with Sinatra’s music and films as jumping off points for reflections on the singer’s successes and shortcomings, including Sinatra’s tempestuous marriage, his rivalry with Bing Crosby, his vocal range and phrasing, and his work as a photographer for Life magazine.

John Brady explores Sinatra’s stormiest romantic relationship, with Ava Gardner, in Frank & Ava: In Love and War (St. Martin’s/Dunne, Oct.). According to Thomas Dunne Books executive editor Peter Joseph, “Brady met Sinatra at Reprise Records; he went on to interview a number of Sinatra’s associates”; these and Brady’s firsthand experience with Sinatra make for a compelling drama of love and emotional war.

Another book from St. Martin’s is by photographer David Wills, who explores Sinatra’s five-decade-long film career in movies such as Anchors Aweigh, Ocean’s 11 The Manchurian Candidate, and Von Ryan’s Express in The Cinematic Legacy of Frank Sinatra. Wills’s book includes more 200 photos as well as essays by Sinatra’s children, Nancy Sinatra, Tina Sinatra, and Frank Sinatra Jr.

Images of Sinatra carry as powerful a punch as his voice. Andrew Howick, who helps curate and edit one of the world’s largest collections of photos of Sinatra, collects a stunning array of photographs that helped shaped the singer’s persona in Sinatra: The Photographs (Abrams, Oct.). Accompanied by a foreword by Sinatra’s widow, Barbara Sinatra, and commentary by friends and collaborators, these photos depict the Chairman socializing with Bing Crosby, Mia Farrow, Ava Gardner, J.F.K., and Marilyn Monroe, and making music with Nelson Riddle and Quincy Jones.

Charles Pignone (The Sinatra Treasures) gathers more than 400 illustrations in color and black-and-white—many never before seen—as well as unpublished personal interviews with Sinatra and his family and friends, in Sinatra 100 (Thames & Hudson, Oct.), with forewords by Tony Bennett and Steve Wynn.

Perhaps the biggest gift of all for fans—and for Sinatra’s memory itself—is Sinatra, compiled by Amanda Erlinger and Robin Morgan (ACC Editions, Oct.), an art book filled with previously unpublished photographs, taken and authenticated by Nancy Sinatra and with a print run limited to 1,000 copies, at $1,500 each. “Sinatra is undeniably the ultimate pop icon of all time,” said Sudha d’Unienvillle, v-p of ACC Art Books.