“It is with great sadness that we inform you of the passing of Jimmy on the evening of July 6. The family appreciates the outpouring of love and heartfelt condolences and asks that you continue to respect their privacy during this difficult time,” Caan’s official account posted Thursday morning. “End of tweet.”

As an octogenarian using Twitter, James Caan maintained a healthy sense of humor about his relationship with social media and technology, finished every post — mostly featuring photos from his illustrious, six-decade run in Hollywood, but occasionally random pop culture musings and amusing words of wisdom — with the on-the-nose sign-off, “End of tweet.”

It became a late-career calling card for the distinguished performer, and one his family continued until the very end.

The Bronx-born, Queens-raised actor appeared in more than 90 films after making an uncredited appearance as “Soldier With Radio” in Billy Wilder’s 1963 rom-com Irma la Douce, starring Jack Lemmon and Shirley MacLaine.

His first substantial role came a year later, playing a hoodlum who gets his eyes poked out opposite Olivia de Havilland in the dark thriller Lady in a Cage. It would also be the first of countless “toughs” Caan would play over the next half-century.

Bold-faced filmmakers were drawn to his soulful machismo from the get-go. Howard Hawks gave Caan his first leading role in the car racing drama Red Line 7000 (1965), then cast him again alongside John Wayne and Robert Mitchum in the 1966 Western El Dorado. Robert Altman hired Caan for his second feature, 1968’s sci-fi picture Countdown, with his future Godfather co-star Robert Duvall.

No early-career relationship, however, was as fruitful as the one Caan forged with one of his classmates from Hofstra University, Francis Ford Coppola.

After enlisting Caan to play a brain-damaged football player in 1969’s The Rain People (two years before Caan would earn an Emmy nomination for starring in one of the most beloved TV films of all time, the gridiron man-cry favorite Brian’s Song with Billy Dee Williams), Coppola gave Caan an offer he couldn’t refuse, to play the hot-headed, ill-fated gangster Sonny Corleone — brother to Al Pacino’s Michael and son to Marlon Brando’s Don Vito — in the all-time classic, 1972’s The Godfather.

Caan earned his first and only Oscar nomination for the role — and would be closely associated with the role for decades to come.

“I won Italian of the Year twice in New York, and I'm Jewish, not Italian,” the actor once mused.

“Jimmy was someone who stretched through my life longer and closer than any motion picture figure I’ve ever known,” Coppola said Thursday in a statement to Deadline. “From those earlier times working together on The Rain People, and throughout all the milestones of my life, his films and the many great roles he played will never be forgotten. He will always be my old friend from Sunnyside, my collaborator and one of the funniest people I’ve ever known.”

“Jimmy was my fictional brother and my lifelong friend,” Pacino said in a statement, also via Deadline. “It’s hard to believe that he won’t be in the world anymore because he was so alive and daring. A great actor, a brilliant director and my dear friend. I’m gonna miss him.” Robert De Niro, who played a young Vito Corleone in The Godfather Part II, added simply, “I’m very very sad to hear about Jimmy’s passing.”
The Godfather launched Caan to new heights. He played the title part in the 1974 James Toback-written drama The Gambler. That same year he co-starred with Alan Arkin in the offbeat buddy-cop comedy, Freebie and the Bean and briefly reprised Sonny for a flashback in The Godfather: Part II. He scored hits with the Barbra Streisand-starring musical Funny Lady (1975), Norman Jewison’s fast-skating Rollerball (1975), and Sam Peckinpah’s actioner The Killer Elite (1975), re-teaming him with Duvall.

Caan directed the only film of his career with 1980’s Hide in Plain Sight, a drama in which he also starred as a man who suspects his missing ex-wife and children are now living in a witness-protection program.

Besides The Godfather, Caan’s favorite film was Michael Mann's 1981 neo-noir thriller Thief. Caan starred as a professional safecracker trying to leave behind a life of crime.

"What a terrible and tragic loss," Mann said in a statement Thursday. "Jimmy was not just a great actor with total commitment and a venturesome spirit, but he had a vitality in the core of his being that drove everything from his art and friendship to athletics and very good times. There was a core of values within him about how people should be, more or less. It might be variable, the corners could be rounded with urban irony, but there was a line and it was non-fungible. And it produced many outrageous and hilarious anecdotes.

"I loved him and I loved working with him. He reached into the core of his being during difficult personal times to be the rebellious, half wild child, institutionalized outsider Frank, in my first film, Thief. Frank is half Frank, half Jimmy. The character and the man — like his Sonny in The Godfather — were made for each other."

Caan became disillusioned with acting in the 1980s, particularly after a negative experience on 1982’s Kiss Me Goodbye. He took six years off from acting, a period in which he suffered from depression over his sister’s death from leukemia and developed a cocaine addiction.

Caan returned to the screen in the 1987 Vietnam drama Gardens of Stone and drew praise for his barely recognizable turn under heavy prosthetics in Warren Beatty’s 1990 mob comedy Dick Tracy.

However, Caan credited his comeback to Rob Reiner. The filmmaker's 1990 Stephen King adaptation Misery starred Caan as bedridden author terrorized by an obsessed fan (Kathy Bates). As Bates and Reiner recalled to Yahoo, the two leads clashed during the film, which Reiner encouraged them to channel into their performances. Bates wound up winning an Oscar for her role.

In a statement Wednesday, Reiner fondly remembered Caan. “I was so saddened to hear about Jimmy leaving us. I loved working with him. Besides being a talented instinctive actor, he was the only Jew I knew who could rope a calf with the best of them. Sending my love to his family.”

Caan continued his second with act by displaying his comedic chops — while playing a gangster again — in the 1992 hit Honeymoon in Vegas opposite Nicolas Cage and Sarah Jessica Parker.

Nearly a decade later Caan would deliver perhaps his most memorable comedic turn, as the cynical kids lit exec who discovers he has an adult son, raised by Santa in the North Pole, in the Will Ferrell-starring contemporary Christmas classic Elf (2003).

Other recent film and television roles include Dogville (2003), Las Vegas (2003-2007), Get Smart (2008), Cloudy With a Chance of Meatballs (2009) and That’s My Boy (2012). One of Caan’s last roles, in the Philip Noyce-directed mob drama Fast Charlie co-starring Pierce Brosnan, is currently in post-production.

"I want to do a good piece of work," Caan told CBS This Morning’s Ben Mankiewicz in 2021, noting his he wasn’t ready to retire. "I'm frustrated. I'd love to do a real character thing."

This tributes have poured in as news of Caan's death spread.

“We were lucky enough to work with James Caan on Cloudy With a Chance of Meatballs,” tweeted the film's co-director Chris Miller. “He brought a pathos and authenticity to the role of Tim Lockwood that held the film together. RIP to a legend.”

“James Caan. Loved him very much,” wrote Caan’s That’s My Boy costar Adam Sandler. “Always wanted to be like him. So happy I got to know him. Never ever stopped laughing when I was around that man. His movies were best of the best. We all will miss him terribly. Thinking of his family and sending my love.”