Charlie Holland turns 93 years old Friday. “I am so old my social security number is two,” he quips.

Just two weeks earlier, Holland had played to yet another packed house with his band, The Charlie Holland Band. On this occasion, the venue was the Stonington Harbor Yacht Club, one of many places his group has graced over the course of the past six decades. Whether his band was playing at Groton Motor Inn, The Harbor House, Water Street Café (where his portrait hangs on the wall), or, most notably, at the old Skipper's Dock where the band held forth every Sunday afternoon for 30 years, a faithful and adoring crowd was in attendance. That adoration is largely due to the bandleader himself.

Charles Braton Holland was born in Westerly on July 20, 1925. Calvin Coolidge was sworn in to his first full term as president that year. Babe Ruth was in a slump after batting .378 with 48 home runs in the 1924 season. George Gershwin’s "Rhapsody in Blue" was first performed in New York the previous summer. F. Scott Fitzgerald published "The Great Gatsby" in April. It was the Jazz Age.

Holland was born to Charles Braton Holland Sr., who was raised in Stonington and employed by Electric Boat, and Alice Sullivan, a homemaker. Together they raised five children, including Charlie’s brother Ron, who went on to a successful career as a Madison Avenue advertising executive. Charlie was 13 years old when the Hurricane of 1938 struck the region, resulting in 687 deaths and 57,000 homes damaged or destroyed by the storm. The greatest impact was on Rhode Island. Holland recalls being a Boy Scout at the time and being sent out to Misquamicut Beach with his troop to recover dead bodies.

Holland grew up in Pawcatuck and attended local schools. Then, on Dec. 7, 1941, the Japanese attacked Pearl Harbor, and Charlie entered the Army on Sept. 2, 1943. During the war, Charlie served as a tail gunner with the Army Air Corps and flew on 18 B17 missions over Germany, Holland, France and Belgium. After his discharge in March 1946, Holland attended Syracuse University in New York on the GI Bill, where he studied English literature. He subsequently completed his degree at the University of Rhode Island.

Charlie’s love of music, particularly traditional jazz, came early. He had grown up in the great jazz era of Louis Armstrong, Duke Ellington, Bennie Goodman, Roy Eldridge and Coleman Hawkins.

"I had friends in high school that played jazz. So I decided to take piano lessons," Holland recalls. "The lessons cost 50 cents. I quit. I couldn’t afford it. I am largely self-taught.”

He formed his first band while still in high school, the eponymously named Charlie Holland Band, with Charlie leading the ensemble on piano. The band has retained that name for 75 years. Today, Holland’s bandmates include Dom Perrone, trumpeter, age 90, who has been with the band for 50 years, and Zeb Gnocche, clarinetist, age 92.

As great as Holland’s passion for music is his passion for great writing and classic literature. Holland favors late 19th- and 20th-century British novelists Somerset Maugham, Thomas Hardy and Virginia Woolf. Among American writers, Holland has an affinity for Thomas Wolfe, Ernest Hemingway and F. Scott Fitzgerald.

Holland raised a family in Pawtucket with his wife Martha (Moorhouse), now deceased, and has two grown daughters, Martha Ann, who resides in New York City, and Margaret, who lives in Boston. Although Holland “retired” from his position as a “road man” for Chrysler many years ago, he has hardly retired from his daily pursuits. Today, Holland lives on his own above Tom’s News in Stonington Borough, and follows a daily routine including lunch at The Dog Watch Café, mid-afternoon at Breakwater (the old Skipper's Dock), happy hour at Noah’s Restaurant, and a nightcap at Water Street Café. Holland can be seen with his customary lunch martini at The Dog Watch and his Dewar’s nightcap at Water Street. When the weather is nice, he can be seen with his latest book (he still reads over a dozen each year) on the bench in front of Tom’s News. “I’m a slow reader,” he claims.

In addition, Holland continues to take great pride in his 1997 Blue Jaguar, which he drives to and from lunch each day.

Charlie Holland has seen a lot in his day. He has lived through 15 presidential administrations. He says his favorite president was Harry Truman. He attended the famous Ali-Frazier heavyweight title fight at Madison Square Garden in 1971. He has played with his band at the Four Seasons in New York, as well as at the Ocean House in Watch Hill. He has learned and told more jokes than Henny Youngman, his favorite comedian, whose comedic style he echoes. And, through it all, he has retained his great humility.

For his 93rd birthday, Charlie Holland’s friends and neighbors will be feting him at the Mystic River Yacht Club.

“It’s my hobby," he says of why he still plays. "It keeps me busy, gives me something to do. I enjoy playing music, and I enjoy playing with my friends. We’re the same age, you know.”

If it’s like any other occasion, Charlie will be the sharpest eye and the sharpest mind in the house.

Randy Bean is an author and contributing guest columnist to publications including Forbes, Harvard Business Review, MIT Sloan Management Review, and The Wall Street Journal. You can contact him at rbean@newvantage.com and follow him at @RandyBeanNVP.