In a room adorned with icons of 1940s pop culture — a Casablanca poster, a framed record of Frank Sinatra’s Come Fly With Me, photos of Dean Martin and Elvis, and a door-sized print of “V-J Day in Times Square,” to name a few — Zack Alexander feels right at home. “This is the only area in the house that’s attractive enough for an interview,” he jokes.
A New Jersey native, Zack Alexander is a 21st-century crooner: the 2016 Hoboken Sinatra Idol winner, a Big Band aficionado, and a devoted interpreter of the Great American Songbook. Jazz enthusiasts from across the state gather ’round to hear him deliver classics like “I Get a Kick out of You,” “My Way,” and the timeless “I’ve Got You Under My Skin.” Alexander is dedicated to keeping the Songbook alive, and he thrives on the connections he makes with new listeners and seasoned devotees.
I chatted with Alexander about his musical origins, his favorite performances, and how he’s helping new generations fall in love with jazz.
Since you often tour around New Jersey, is there a particular Jersey audience that has been the best?
Zack Alexander: I live in Red Bank, but I’m based out of the Jersey Shore, and because of the music that I do, it tends to lean toward an older crowd. I am still shocked to this day that people go out on a Tuesday or a Wednesday. These people are so much fun; when you’re younger, you think to yourself, “I don’t want to get old,” but these people are living life to the fullest. They really enjoy what I do, and their support means everything to me. One town in particular that I’ll always call out is Spring Lake. Spring Lake has been so good to me over the years. I’ve performed at the Breakers in Spring Lake, as well as Amelia’s by the Sea next door. The Essex and Sussex a little bit further down the road is a 55-and-over community that has me all the time. I was there this Halloween as well. They recently brought back their costume party, and they thought who better than me to come in and do what I do best, and sing and entertain the crowd. That community, particularly, and that crowd has been so good to me.
Let’s go back to the beginning. What was your very first exposure to jazz? Did you have a favorite song to sing?
ZA: I come from an Italian-American household, so Frank Sinatra, Dean Martin, and Tony Bennett were playing nonstop growing up, and I fell in love with it. That first song, “Summer Wind,” is always going to be near and dear to me. It’s a favorite of mine. I heard it from my grandmother. She played it on a 45, and I was hooked ever since. One song that I really like to perform is “I’ve Got You Under My Skin” by Cole Porter. It’s just a favorite of mine for many reasons, but one, Nelson Riddle, who orchestrated it and arranged it for Frank Sinatra, is also from New Jersey.
There’s a lot of talent in New Jersey, I must say! Frank Sinatra and Nelson Riddle collaborating together is just magic. That specific arrangement, Nelson Riddle finished on the way to the studio with a flashlight and a pencil while his wife drove. The lore and the story behind that song, as well as the orchestration and the magic that occurs between Sinatra’s vocals and Riddle’s arranging talent, makes me feel stellar. It’s electrifying when I do that song.
Your jazz career didn’t start until you were 16. Were you singing a lot in the years prior, or was it something that snuck up on you?
ZA: I’ve always sung since childhood. I was in the school choir, and I did one or two performances in musical theater in high school. I got my start where every singer gets their start: in the shower. Then it just grew and grew and grew. I started singing at family parties. My parents were impressed because no one knew I could sing. I would keep it very private. I would do choir, but it’s always in the background. I was never featured up front doing my thing. Once I started performing at family parties, they strongly encouraged me to audition for shows and try to make something of it. Now I do it full time, so it’s definitely a blessing, that’s for sure.
Your first public singing appearance was at one of these family parties. Did that surprise everybody? What was the reaction?
ZA: We threw this 1970s themed party in our backyard, and my whole family was there. I was in a leisure suit, everyone’s dressed up in disco attire, we’re playing like the Bee Gees, and having a blast. My uncle was playing the guitar, and a few other family members were doing karaoke. I said, “You know what, I’ll go up and sing.
”I wanted to sing something that was like prominent from the 1970s, and I had been listening to Jack Jones perform the theme from the Love Boat TV show, so I sang the theme, and everyone was shocked. I had one uncle lean over to my dad — there’s footage somewhere out there, horrible cell phone footage from way back when — and I heard him say, “Wow, he’s actually good!” They weren’t expecting it to come out of me, and everyone was impressed and very complimentary. They all encouraged me to really pursue this.
Did your family know that you had been quietly studying the Rat Pack at that time?
ZA: No, not really. I kept it to my bedroom — it’s my little sanctuary of all of my favorite things. I would turn on the TV, I’d go on YouTube, and I would watch all sorts of performances. I have a full-length mirror on the opposite side of my room, and I would stand in front of the mirror, because I noticed that other performers from back then, the crooners, had a way about them; the way they move, the way they hold themselves on stage. Because I am meticulous when it comes to those types of things, I wanted to watch myself as I sang. I really did keep it to the bedroom for many, many years, until I was ready and felt comfortable enough to try to do it in front of other people.
jazz and the Great American Songbook; it’s a treasure trove of all sorts of great music.
What about the style of the crooners makes them a little bit more unique to the average listener who may not know a lot about that style?
ZA: I gravitate toward that style because of how it really just makes me feel. There are so many levels of emotion, especially with the Great American Songbook. That is the crux of what I do and the genre that I dedicate my whole life and soul to. It’s the one thing that could never hurt me, jazz and the Great American Songbook; it’s a treasure trove of all sorts of great music.
The way the crooners sing and their style has this range of emotion. You can have this tender, beautiful ballad, or a soaring power ballad, or a swing tune that just drives with a band, and it sounds like a lot of fun, and it has this warmth to it. There’s a smoothness to it that I think makes it, if you were to categorize it into something other than jazz, kind of like easy listening. Most people can sit down and understand the words and identify with the feelings and their style, and the lyrics are timeless. It just has this feeling of relaxation for me at least, when I hear that style rather than everything else. That’s the power of music; it evokes different feelings for different people. If I want to rock out and go crazy, I’ll go for Ozzy Osbourne or Led Zeppelin, but if I want something relaxing and easy to listen to, it’s always going to be Frank Sinatra or Tony Bennett.
Tell me a little bit about Hoboken Sinatra Idol! What was that whole process like? Did your win surprise you at all?
It’s stiff competition — it’s Hoboken, and they know their Sinatra, that’s where he’s from!
ZA: They hold that competition still to this day, and I’ve been so involved with their historical society and their museum that they have now asked me to be a judge, so now I sit on the panel!
It was 2016 and I had just turned 20, but in 2015, it was Frank Sinatra’s 100th birthday, and I just missed the cutoff to send in an audition to be in the competition. They saw my tape, and they said, “Why don’t we give you the opportunity to perform?” They were allowing Sinatra style or crooner type singers to go around the entire city and pay tribute to him in local establishments, regardless of whether you were in the competition or not. They let me do that, then next year in 2016, I auditioned and I got in. Now I think it’s called the Hoboken My Way Sinatra Sing-Off, because American Idol got wind of it. It’s stiff competition — it’s Hoboken, and they know their Sinatra, that’s where he’s from!
I was also one of the youngest, if not the youngest competitor. Most of the guys were in their 40s, 50s and older. I think last year they actually had a 10-year-old, which was so cute. To be able to sing his music in his hometown, in front of people that knew him, was just absolutely thrilling. I sang Cole Porter’s “I’ve Got You Under My Skin.” Later on, out of curiosity, I looked up Cole Porter — the contest that day happened to fall on Cole Porter’s birthday, so I was like, this is fate! I won, and I got a perfect score, which I’m beyond proud of. That really set the tone for the upward motion of what I’m doing. That competition led to one gig, which led to another, which led to my North Jersey crowd. I’ve got a Hoboken crowd that are regulars.
What’s interesting, oddly enough, like the Essex and Sussex down in Spring Lake, a lot of that crowd has overlap. Some of them will have apartments in Hoboken, as well as their unit in Spring Lake, and I will run into people and say, “Oh, I didn’t even know you were up here!” New Jersey, as large as it is, is a small town. Everyone knows everyone, especially in the jazz and Sinatra community.
You’re involved with the Rat Pack Alliance. Have you gotten the chance to collaborate with anybody through that organization, whether it be someone on a larger scale or someone of a more local scale?
ZA: Karen Morris runs the Rat Pack Music Alliance, and she has done so many events and different things over the years. I still do events with her — we have one coming up in Avon-by-the-Sea on Dec. 6 — and it’s always a Sinatra tribute. She is a delight to work with, she’s been fantastic. The other person that I’m thrilled that I got to work with was actually Dean Martin’s daughter, Deana Martin. I sang with her at the Count Basie Theatre, we did a Sinatra tribute of course. It was such a nice experience to get to meet someone, not only in the world of that, but to be actually related to one of those greats. It was great to talk to her and hear different stories — she calls Frank Sinatra “Uncle Frank.” That was also through the Red Bank Jazz Orchestra and the Jazz Arts Project, which is a nonprofit organization that tries to expose younger people to jazz and put instruments in their hands.
You’ve segued nicely into my next question: how are you finding ways to connect the Great American Songbook to younger audiences? Through that, with this being “Out In Jersey,” do you find that there’s a connection to be made with the Songbook and younger queer audiences?
ZA: I’ll bring it back to Cole Porter. Cole Porter is one of the most legendary gay songwriters, and he really paved the way for a lot of people, especially in a time when it wasn’t okay, or socially acceptable, I should say. But whether it’s 1925 or 2025, the music is timeless, and I do think that it does resonate with younger people. I’ve done a lot of weddings, I’ve done gay weddings, I’ve done plenty of straight weddings, and it’s younger people, and they hire me to do their cocktail hour.
The reason that I like it so much is that it gives me faith that there is a younger audience, but in addition to that, what I really like about it more is that they tend to tell me that the reason that they’re hiring me may not necessarily be because they love the music, but because it reminds them of their grandparents, or their parents, or people that have since passed and couldn’t be at their wedding. It is really about that connection to this family feeling; it’s warm, it’s fuzzy, and that’s really what I like about it. I do think that younger people are starting to identify with it and relate it back to generations from before, and I’m one of them.
What can we expect from you next?
ZA: Other than my regular tour, which I call my “Restaurant Tour,” the big upcoming thing that I have, that I absolutely cannot wait to do, is at the Algonquin Arts Theatre. It’s a holiday show on Dec. 21 at 3 p.m.. It’s going to be a mixture of Sinatra, because he was born on Dec. 12, and holiday classics. I have a 10-piece band with me from Manhattan coming in; they’re technically Jersey-based, but they play at Swing 46 in Manhattan. Tickets are selling very well, thank goodness, but there are still tickets available, and I would love for as many people to come out and see it. I was there around Valentine’s Day two years ago now, and it was a sellout, it was huge. It’s hard to even put into words how I felt, to just feel that collective support for not only me, but the music in general. I’m a very cynical person, but this job has really turned my viewpoint around, because I have met so many kind people over the years.
Other than that, I have different things at 55-and-over communities coming up, different big parties and events where I perform. Normally, I don’t sing with a band; most of the time, it’s just with band tracks. When I do perform, I’ll either perform with Swingadelic, the band that I’m playing with in December, or I’ll perform with a 17-piece band called Swingtime Big Band. We have Veterans Day shows coming up in November out on Long Island. The band as a group itself has been around for like 50 years. Throughout the years, they changed leaders, and my band leader is now in charge of it. We love making music together.
If you could bring back one Rat Pack member and sing one song with them, who would it be, and what would you sing?
ZA: Well, the obvious answer is Frank Sinatra. I would love to be able to sit down and just have a conversation with him about all of this. He actually loved big band music, aside from his own catalog. He once said, “All I want for a birthday gift is to have a big band in front of me, and me sitting in a chair in a room alone to appreciate and listen to.” And I don’t know if that actually ever happened, but I know for a fact that they had plenty of parties where he was able to sit there and enjoy it. And I agree, reading him say that, I thought, “Me too.”
That’s why I love going to those rehearsals with my band, because that’s essentially what I do. I sit in the corner until it’s my turn to get up and sing, but they do instrumentals as well, and I get to sit and appreciate it. So I think I’d bring back Frank Sinatra. The song we would do would have to be something big. I don’t want to sound cliché and say “New York, New York,” but if he and I did that, it would be explosive. The other one that comes to mind is Dean Martin. And again, not to sound cliché, he and I doing “That’s Amore.” First of all, even if you’re not Italian, every single person, anytime that song comes on, the entire place breaks out into song. They sing along and they all sway and hold hands and people spin napkins. And it doesn’t matter who you are or where you’re from. It’s all about inclusivity and togetherness.
Anything else you’d like to add?
ZA: The only thing that I wanted to add is that I have an unofficial theme song. My theme song, more recently than not, is a song by Sammy Davis Jr., who would have been 100 years old this year. But the theme song is “I’ve Gotta Be Me.” And I’ve always lived by that motto. If I’m not doing myself, then it’s not right. And that’s pretty much the opening line of the song. “Whether I’m right or whether I’m wrong, whether I find a place in this world or never belong, I’ve gotta be me.” And that is everything. That means everything to me. That’s exactly how I live.
