Submitted photo Tony DeSare will perform the songs of Frank Sinatra and some originals as well when he joins the Youngstown Symphony Orchestra for a pops concert Friday at Stambaugh Auditorium.

For Tony DeSare, it all started with a cassette from a drug store.

“I was getting into jazz, so I was playing piano and starting to sing,” DeSare said during a telephone interview. “My mom brought home, I think she got it at CVS or Walgreens, a cassette called ‘Frank Sinatra Gold.’ I guess she saw it and thought maybe I’d like it. I started listening to it, and I just became obsessed. It was all this music that I didn’t know existed. I love the songs. I love the way the recording sounds. I love his voice. And I just started to buy (more). Anytime that I had an extra $15, $20, I would get another Sinatra CD.

“In a way, I’m envious of the kids now that can just, if they think they are interested in Frank Sinatra, they could listen to his entire catalog for free on YouTube or whatever. Back then, before I could hear more, I’d have to get more money and go to the store. But I ended up, I think, during those couple years, accumulating like 150 different things of Sinatra. I really just studied his whole catalog. I just loved it so much.”

The singer and pianist writes and records his own songs. He had four top 10 albums on the Billboard jazz chart, appeared on “A Prairie Home Companion” and “The Today Show” and played venues ranging from jazz clubs to Carnegie Hall.

And for more than a decade, he’s been playing pop concerts featuring the music of Sinatra with such ensembles as the Cleveland Orchestra, New York Pops, San Francisco Symphony and Chicago Symphony.

He’ll add the Youngstown Symphony Orchestra to that list when he performs Friday at Stambaugh Auditorium.

Orchestral arrangements of 20th and 21st century popular music frequently are programmed by classical orchestras. DeSare said what makes his “Sinatra & Beyond” show different is that these songs originally were recorded with an orchestra backing the crooner.

“The music was written to be performed live with an orchestra,” DeSare said. “Unlike most other genres, what we’ll be able to create on stage is the same way that Sinatra recorded this stuff, so you don’t have to leave anything out.”

Sinatra (1915-1998) started his career singing with the Harry James Orchestra in the late 1930s and gave his last public performance in 1995. DeSare’s favorite Sinatra era is 1953 to 1960, when he was on Capitol Records. Not only was he making iconic albums such as “In the Wee Small Hours” and “Songs for Swingin’ Lovers,” he also was prolific, releasing multiple albums each year.

DeSare didn’t have an underrated favorite among Sinatra’s songs, but he said 1957’s “Close to You” is Sinatra’s most underrated album.

“It’s him with the Hollywood String Quartet,” DeSare said. “He always recorded with big orchestras and big bands, and this was just the string quartet with a couple other instruments. His voice is at its absolute peak. The songs are great. Nelson Riddle did the arrangements. It’s something that wasn’t even available on CD back when I was first collecting, so I knew it was out there but I never had it. Then, I finally got it years later, and it’s one of my favorites. It’s in my top three of all time.”

DeSare draws on that knowledge for “Sinatra & Beyond.” In addition to being a performer, DeSare also sees his role as curator, picking a program that he believes the audience will like even more than the songs they might have requested in advance.

“I want somebody that really is a big Frank fan to come in and enjoy it, and I want somebody who barely knows anything about him to really enjoy it,” he said. “That’s the challenge of putting the show together. And I wanted to capture the vibe of what it felt like to go see him live without doing an impersonation.

“I think that really devalues things when people are looking at it through the lens like, I’m trying to be him. I’m not trying to be Frank. But I really studied his phrasing. Our voices are similar, but I do a couple of my own songs in the show, and I’ll play piano as well. So I’m ultimately a different artist than Frank … I can pay tribute to an artist and still have it be from my point of view.”

For “Come Fly with Me” and “Fly Me to the Moon,” DeSare uses the same arrangements Sinatra did. For others, such as “Just in Time” and “Day In, Day Out,” DeSare created original arrangements.

“It’s a love fest for Sinatra, and it’s entertainment too,” he said. “It’s not song after song. Everything’s interwoven with stories and things about the songs. I think sometimes the perception of orchestra concerts is that they can be kind of dry and boring, and the vibe to this is more like, yes, it’s a sophisticated orchestra show, but it’s also kind of like a Vegas 1965 show as well.”

If you go …

WHAT: “Sinatra & Beyond” — Youngstown Symphony Orchestra with Erik Ochsner, conductor, and Tony DeSare, vocalist

WHEN: 7:30 p.m. Friday

WHERE: Stambaugh Auditorium, 1000 Fifth Ave., Youngstown

HOW MUCH: Tickets range from $20 to $65 and are available online at experienceyourarts.org and by calling 330-259-9651.