As the son of one of the greatest guitarists in jazz history, Bucky Pizzarelli, you might say that John Pizzarelli is a natural-born swinger. The popular and prolific guitarist/singer, appearing on Friday, Oct. 17 at Somers Point’s Gateway Playhouse as part of the South Jersey Jazz Society’s Jersey Fresh jazz@thePoint Festival has been swinging since he first started playing guitar at the age of 6.

It’s not that he bypassed pop, fusion and rock. It’s important to note that he’s recorded with Paul McCartney, produced James Taylor’s Grammy-winning album, “American Standard,” and appeared on a number of other recordings with Taylor. He listened to Billy Joel and Bruce Springsteen while growing up, but he was grounded in straight-ahead, mainstream jazz and the Great American Songbook from the start. Presumably, it’s simply in his musical DNA.

Pizzarelli, who studied formally at the University of Tampa and William Paterson University, names Nat King Cole, the great and influential jazz pianist and hit-making singer, as a major influence. But he’s pretty clear that his main influence was his father.

“He was such a good musician, and he was also a good road rat,” Pizzarelli recently told writer Glenn Rifkin of Boston’s The Arts Fuse magazine. “He was the right guy to teach me everything. He was so well-respected.

“On my first record, ‘My Blue Heaven,’ with my father and me, we had bassist Milt Hinton, Connie Kay, the drummer from the Modern Jazz Quartet, horn player Clark Terry, and Dave McKenna, that great Boston piano player. You can’t get those people unless they like my father,” Pizzarelli continued. “All those things were so important in learning what the business was supposed to be like. It was part of the foundation. And he led me to Nat King Cole, which was key.”

Pizzarelli’s experiences over the span of five decades of professional playing have been singular. How many players living today can say they played with the legendary clarinet player and band leader Benny Goodman in Goodman’s living room? Pizzarelli did.

“I got to see a lot of Benny Goodman concerts in New York City,” he told Glenn Rifkin. “Goodman was a regular fixture in my father’s life. When he did a concert at a theater in Nanuet (N.Y.) one night, he came over to our house afterwards. That was pretty wild. Bucky and I opened for Benny on a number of occasions. It was quite special to have done that. I actually got to play with Goodman in his living room. It was me and my dad and Benny, and we just played in his living room. Amazing.”

Though he’s recorded dozens of albums and has worked with everyone from Rosemary Clooney to the Boston Pops, one of the undeniable highlights of his career was in the summer of 1993 when he opened for Frank Sinatra. Pizzarelli wrote beautifully about this precious time in “World on a String: A Musical Memoir,” his vastly underrated 2012 autobiography.

“I was honored to open for him with my quartet in Europe and around the States,” Pizzarelli recalled. “Frank would appear in the wings during our final number, swinging and clapping and smiling. He would come onstage and cheer for us. It was an honor to play with him, and we were thrilled he enjoyed our music.”

So influential was Sinatra that Pizzarelli recorded two albums dedicated to him, “Dear Mr. Sinatra,” with the swinging Clayton-Hamilton Jazz Orchestra; and “Sinatra & Jobim @50.” He’s also done a number of “Dear Mr. Sinatra” stage shows.

“Frank has always been one of my main musical influences,” Pizzarelli has said. “I love the way he transforms himself from song to song.”

The passion, love and respect he has for Sinatra’s music are clear and evident. Even hard-boiled critics have deemed his Sinatra projects as “the most personal of all the Sinatra tributes available.”

As a performer, Pizzarelli is grounded in the show business tradition. He’s engaging, funny, witty and he relates to the audience, which is why he’s one of the few in the world of jazz who has managed to appeal to wide audiences of all ages who may not have liked jazz before they heard him. That’s why, in any given month, he can be heard at venues ranging from the posh Café Carlyle in New York City, to a jazz club, jazz festival or college campus. And though he may be an entertaining showman, he has never compromised. Like Tony Bennett, his musical standards are high. Every song in his book is, in one way or another, a classic.

As a superior jazzman who also sings and entertains, John Pizzarelli is in good company, historically and otherwise. Nat Cole sang and played piano, as does Harry Connick Jr. George Benson plays guitar and sings, and Chet Baker sang and played trumpet. That’s pretty good company, and John Pizzarelli deserves to be there.

The Rest of the Fest:

The Jersey Fresh jazz@thePoint Festival runs from Thursday, Oct. 16 through Saturday, Oct. 18 at the Gateway Playhouse and Gregory’s Restaurant & Bar in Somers Point. Saxophonist Michael Pedicin Jr. and the quartet open the festival on Thursday at 7 p.m. at Gregory’s. After John Pizzarelli’s show at Gateway on Friday, trumpeter Matt Cappy and his quartet will hold forth at Gregory’s at 9:30 p.m. Headlining the Gateway on Saturday at 7 p.m. is guitarist Howard Paul and the Benedetto All Stars, followed by singer/composer Paul Jost and his quartet at Gregory’s at 9:30 p.m.

Tickets for John Pizzarelli and Howard Paul are available at www.gatewaybythebay.org. Admission for Michael Pedicin’s show at Gregory’s is $15 for South Jersey Jazz Society members, and $20 for non-members. Admission to the Matt Cappy and Paul Jost shows at Gregory’s is free.