The iconic singer's centennial allows those closest to him and his admirers to look his astonishing legacy

If there was anything Frank Sinatra enjoyed more than a stiff glass of Jack Daniels, it was blowing out the candles on his birthday cake each and every year. “He loved his birthdays,” says his daughter Tina Sinatra, who’s been spearheading a number of gala celebrations of her late father’s 100th birthday throughout 2015. “Birthdays, they signify life. And he was very, very Italian and very happy to share and to bestow and to celebrate people and himself.”

To commemorate the Dec. 12 centennial of the most significant pop vocalist of his age, the Sinatra family has shared with PEOPLE some personal and intimate and sometimes very funny – images from the singer’s past. “We have pictures of him that are the silliest things you’ve ever seen about his birthday,” she says.

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1. Sparklers adorn Sinatra’s 42nd birthday cake during the 1957 party at Hollywood’s famed Villa Capri restaurant a favorite for hangout the Rat Pack and A-list stars like James Dean and Marilyn Monroe.

2. In this shot from the mid-to-late 1960s taken at his home in Rancho Mirage, California, Sinatra enthusiastically tears into a present as daughter Tina looks on. “You can see he was just a kid at heart when it came to birthdays and holidays,” she tells PEOPLE.

3. Daughters Tina and Nancy greet Sinatra with kisses outside the Beverly Wilshire Hotel at his 50th birthday party. Sinatra also always made a point to spend his kids’ birthdays with them whenever possible – including shared annual family celebrations for Nancy and his pal Dean Martin, whose birthdays were a day apart.

4. “We all decided to surprise him with presents based on ‘The Twelve Days of Christmas’ song that we kids had recorded for the ‘Sinatra Family Christmas Album,'” remembers Tina Sinatra of this 1968 shot from her father’s home in Rancho Mirage, California. “We did it for his birthday instead of Christmas. We piled all his gifts on him, and then we took the picture. It was hysterical.”

5. A hiply attired Sinatra at his 60th birthday in 1975, marking the milestone with his beloved mother, Dolly Sinatra.

6. Sinatra shows off his sillier side with bows celebrating in the late 1970s with daughters Tina and Nancy at Tina’s Beverly Hills home. “He was so funny,” remembers Nancy. “He would always do silly things like put a box on his head, or ribbons on his face. He was a hoot!”

7. In 1980 the cake for Ol’ Blues Eyes’ 65th birthday featured a toy train-shaped confection traveling across the landscape of one of his “home” neighborhoods, Palm Springs. “He loved model trains, and had quite the collection that he curated over the years,” says granddaughter Erlinger. “People from all over the world would also send him trains.”

8. The Sinatra clan – clockwise from top: Frank Sinatra Jr., Tina Sinatra, granddaughter Amanda Erlinger, Frank Sinatra, granddaughter A.J. Lambert and Nancy Sinatra – gathered at Los Angeles’ L’Orangerie restaurant for the patriarch’s 74th birthday in 1989.