- [Announcer] "Here's the Story."

- [Interviewer] How did the music of Frank Sinatra come into your life?

- Well, that's honestly the number one question that's always asked of me whenever I'm performing anywhere, is how did you get into this music?

It's not common for a 27-year-old that's, one, interested in this music and, two, interested in singing it and performing it.

And the answer to that is always the same: it's my grandmother.

My grandmother, 1920 baby, lived to the age of 99.

We lost her just at the onset of the COVID pandemic in 2019.

And from a young age, I was, well, I was always grandma's boy.

She had helped raise me while both of my parents would work.

And as a member of the Greatest Generation, she would always tell me of singers and big bands of the 1940s, mostly about Frank Sinatra, Perry Como, Tommy Dorsey, Nat King Cole, the greats, and how could you just not fall in love with both the music and the mystique of Frank Sinatra.

[gentle music] - My name's Martin Joseph.

I'm a singer and I live in southern Spain.

- Hi, I'm Steve Cardone in Atlanta, Georgia.

- My name is Robert Kim.

I'm a professional photographer from Los Angeles.

- My name's Chris Patti.

I'm 27 years old.

I'm from Citrus Springs, Florida.

- Hi, my name is Rick Stevenson.

I live in Kingsville, Ontario, Canada, and I am a singer of Sinatra music.

- Good evening.

My name is Tracy Bentley.

I live in Mount Airy, North Carolina, and I work in the automotive industry for the last 30 plus years, and I'm a Frank Sinatra tribute artist.

- I'm Lee Miller.

I live here in Hoboken, New Jersey.

I work as a television director at NBC News for the "Today" show.

And in addition to my work in TV, I also sing as a hobby.

And I love to sing Frank Sinatra songs - During my time at Rutgers University, certainly, you know, hey, I was a big karaoke fan.

I've never been shy about being on stage.

Greetings, PBS, and Mr. Steve Rogers.

I always made a point to, hey, never refrain from being near a microphone.

My name is Fernando Uribe.

I wanna take this opportunity to thank you for giving me some time to share my story and why I'm so excited to participate in the Sinatra Sing-off coming up on Thursday night, June the 22nd, at Sinatra Park in downtown Hoboken.

- My name is Tyler Ricker.

I am 27 years old.

I currently work in retail and I'm loving it.

However, for the last seven years, I have also had gigs serenading the Tri-State area with the sounds of Frank Sinatra, - Frank Sinatra has been a part of my life since I was really young.

I can't even explain why.

It was just something that really struck me from a young age, - If truth be told, I did it on a dare.

I was starting on my life as a professional musician.

And, of course, my career was going nowhere.

So a friend of mine said, "Hey, listen, Rob, they're giving auditions for this new television show, and who knows, you might get lucky, you know?"

So I went down there on a dare and I did my best.

And to make a short story long, I won.

- While all my friends were out playing hockey and rocking their long hair and driving pumped-up Gremlins, I sang Sinatra.

- My mom would always play music while she was cooking.

That's where I got my wide variety of music.

- Singing has always been a part of my life, either in choirs or solo.

- Whether it was listening to "My Way" and what a powerful song it is, you know, you just get to learn about all the triumphs in life and all really, you know, what the losses teach us.

And it's a really just powerful song that I've always enjoyed.

- To this day, there's a few songs that I can't sing publicly, because they bring me tears and remind me of the days when my grandfather used to sing to me - One day, while my mom was cooking, she decided to put on Frank Sinatra.

Right from the minute I heard his voice, I was instantly hooked.

- You see, with every generation, young people have their own forms of music.

You know, you have your Britney Spears, you have rap music, and that's all fine and good.

But there are certain songs, and songs particularly from my generation, you know, music by like Frank Sinatra or Tony Bennett, music that is so beautifully written and so gorgeously produced with such memorable lyrics.

And these songs have been really the signposts of our generation.

And they're so beautiful, songs that you can sing to people, bring back such wonderful memories.

And these are the kinds of songs I like to sing, because they never go outta style.

- It never gets old, because the beauty of the songs, some of which are almost 100 years old, just really stand the test of time.

And every night, I see young couples or old couples holding hands and looking into each other's eyes and being really moved by the music.

And it's a real thrill to be able to do that.

And like I say, it never, ever gets old.

[gentle music continues] - [Fernando] Since 2007, the city of Hoboken, the city of Frank Sinatra, has hosted an annual concert and competition to crown the best Sinatra-style singer.

Performers have come from all over the country and world to pay tribute to Hoboken's favorite son and to see just how big his shoes are to fill.

Despite his passing 25 years ago, Sinatra's long shadow is still cast across the town, and he still calls to the hopeless and the hopeful, the up and the down, the pawn and the king.

But on the day of the Sinatra Sing-Off, it mostly calls to the courageous.

- This is a tough crowd, wow.

Tough judges.

- It's Hoboken.

It's always a tough crowd.

[audience laughs] - [Fernando] You think you got what it takes, kid?

Try making it in Frankie's town.

[patrons chattering] - Ladies and gentlemen, welcome to Ebby's.

My name is Tyler Ricker and I'll be emcee-ing this evening, so sit back, relax, enjoy the delicious Italian fare.

It is Sunday gravy, so please indulge in that, if you so desire.

And let me take you back in time with the sounds of Sinatra.

[upbeat, jazzy music] I live in Manchester Township, New Jersey.

I currently work retail work for Target.

However, for the last seven years, I have serenaded the Tri-State area with the sounds of Sinatra, Dean Martin, Tony Bennett, Michael Buble, a little bit of all of the crooners of yesteryear.

♪ Come fly with me, let's fly, let's fly away ♪ ♪ If you can use some exotic booze ♪ ♪ There's a bar in far Bombay ♪ ♪ Come fly with me, let's fly, let's fly away ♪ When I was a kid, I kind of craved being the center of attention.

That actually kind of went away for a little while.

Like when I got to like middle school age, I'm like, "Is it really cool to be like singing in front of a whole bunch of people?"

But I obviously got over that pretty quickly.

- [Interviewer] When did you get over it?

- I think probably around college is when I kind of broke out of that shell and I kind of regressed back to, "Hey, I like being front and center, doing what I do."

♪ You might hear the angels cheer, 'cause we're together ♪ - I was a little concerned, because I really didn't know how far he was gonna take it.

I didn't expect it to go this far.

And, you know, I was concerned about when he turned 16 and his voice was changing whether he'd still be able to sing.

But he has a beautiful baritone.

♪ Once I get you up there where the air is rarefied ♪ - I was attending Ocean County College right here in Toms River at the time, and I saw a piece of paper, it said tryouts for what they called the OCC's Got Talent.

And I'm like, well, you know, I might as well try it out.

So I went and I auditioned and I originally auditioned with "I've Got You Under My Skin."

And then I thought, "All right, well, maybe that song isn't the right one for me."

So I ended up singing "Come Fly With Me," and it was the first time I was really like on stage singing in front of people, and it was kind of a shock to everybody, like my own father.

I knew I could carry a tune, but he certainly didn't know that I could do that and sing like Frank Sinatra.

But it was nice.

It was 10 years of hard work that I felt paid off, because before that time, it was just me doing that in my bedroom ♪ Come fly with me, let's fly, let's fly away ♪ [audience cheers] Actually leading up to the process of the actual event, like going through weeks of rehearsal, like I was just struck, like scared behind the microphone.

So I didn't know how to like command a stage or anything like that.

And then something went off in my brain the night of, when I was on that stage, and I took off and was able to be an entertainer instead of just a singer.

- [Interviewer] When did that strike?

When you were on stage?

- Yeah, literally as soon as I sang the first verse to "Come Fly With Me," and then I took off and I was, yeah.

And I ended up winning the entire competition.

♪ Come fly with me, let's fly, let's fly ♪ ♪ Pack up, let's fly away ♪ [audience cheers] [gentle piano music] [gentle piano music continues] - Please take a moment to admire the fabulous cake provided to us by the famous Carlo's Bakery.

- Thank you.

But, of course!

- My name is Lee Miller.

I live right here in Hoboken, just a few blocks away.

During the week, I work for NBC News.

I'm a television director.

I directed the "Today" show.

Specifically, it's the fourth hour of the "Today" show with Hoda Kotb and Jenna Bush Hager.

- [Interviewer] Now, were they all aware that you're doing this?

- Uh, no, they are not aware that I'm doing this.

- [Interviewer] So here we are today.

It's the big Sinatra Sing-Off.

Are you nervous?

What are your feelings?

- Oh, if I'm nervous, I feel like I'm gonna have a good show and I am really nervous today.

♪ Fly me to the moon ♪ ♪ Let me play among the stars ♪ - Are you nervous?

- No, no.

I love doing this stuff, so I'm excited.

Got some family and friends coming.

Should be fun time.

♪ Let me see what spring is like on Jupiter and Mars ♪ ♪ In other words, hold my hand ♪ - The people in my high school freshman year thought I was a chain-smoker.

And the only reason they thought I was chain-smoker, smoking cigars, not cigarettes, was because of my father's affinity towards Sinatra and Romeo and Juliet cigars from the Dominican Republic.

My father would drive his Jaguar XJ8, roll the windows down, regardless of summer or winter, bump Sinatra all the way to the top, light a cigar, and drive me to school.

For 15 minutes, it was like the calmest, most serene you will ever see that man ever.

And like my love for the guy just was born from that moment forward.

- Are you nervous?

- I don't think I'm nervous.

I think almost in a way I kind of just want it to be over, but in a good way.

Like I'm very excited for everything to come.

But the buildup is starting to get to me a little bit.

♪ And now the and is near ♪ - I'm only ever nervous if there's something wrong physically, you've got an infection in your throat or you don't really know the song.

♪ And so I face the final curtain ♪ But if I don't don't know "My Way," then there's something seriously wrong.

♪ My friends, I'll say it clear ♪ ♪ I'll state my case of which I am certain.

♪ Okay?

[gentle music] [audience chattering] [gentle music continues] - Is everybody here?

Is everybody here?

- [Contestant] Yeah, I think so.

- Okay, so Geri's starting and then she's gonna gimme the heads up and then she wants you all guys to come in together, okay?

So I'll give you... Not in the order, it's just to kind of introduce everybody.

- We bring these in with us though, right?

Our numbers?

- Yeah.

Yeah - Okay.

- So I'll give you the heads up when she gives it to me, but just everybody stay in here for now, okay?

- It's a singing contest, but it's specific.

So like, unlike "American Idol," where I'm sure contestants are singing different genres, our contest is specific to Sinatra.

Sinatra-style singers is what I would call it.

I don't really call them impersonators.

So we are looking for, say we have 12 or 15 contestants, we're looking for the best Sinatra-style singer.

And that would mean, you know, we would include everything, the dress, they would also have to have good singing ability, but also the phrasing of Sinatra, the style of his singing, maybe the chutzpah that he would have when he would perform, you know, the intimacy that he would project into the music.

So that's kind of what we're looking for.

- It's right back lead off.

You know what, I'm happy sitting at the table.

Absolutely.

- [Geri] On behalf of Mayor Ravi Bhalla and the city of Hoboken, I wanna welcome you to another Sinatra Sing-Off!

[audience cheers] We're in the beautiful Kissinger Room of- - You know, when you do this a lot and you feel like you're doing what you were made to do you don't get nervous, you just, you get excited.

So yeah, it's gonna be fun.

[swinging big-band music] ♪ That's life ♪ ♪ That's life ♪ ♪ That's what all the people say ♪ ♪ You're riding high in April, shot down in May ♪ ♪ But I know I'm gonna change that tune ♪ ♪ When I'm back on top, back on top in June ♪ ♪ I say, that's life ♪ ♪ That's life ♪ ♪ And as funny as it may seem ♪ ♪ Some people get their kicks ♪ ♪ Stomping on a dream ♪ ♪ But I won't let it, let it get me down ♪ ♪ 'Cause this fine, old world keeps spinnin' around ♪ [upbeat, jazzy music] ♪ Someday, when I'm awfully low ♪ ♪ When the world is cold ♪ ♪ I will feel a glow just thinking of you ♪ ♪ And the way you look tonight ♪ ♪ Best is yet to come and, babe, won't that be fine ♪ [sultry, jazzy music] ♪ You think you've seen the sun, but you ain't seen it shine ♪ ♪ Wait till the warm-up's underway ♪ ♪ Wait till our lips have met ♪ ♪ Wait till you see that sunshine day ♪ ♪ You ain't seen nothin' yet ♪ ♪ Here's to those ladies and the gentlemen ♪ [upbeat big-band music] ♪ Here's to the AF of M ♪ ♪ I wouldn't have made it without them ♪ ♪ Here's to the band ♪ [audience cheers] ♪ Here's to the band ♪ [audience applauds] - [Rick] Thank you very much, very kind.

Thank you.

- [Geri] So, Gary, who do we have left?

- Our next contestant is Tyler Ricker from Whiting, New Jersey.

[audience cheers] - How are y'all doing tonight?

So my name is Tyler Ricker.

I hail just west of the Jersey Shore, and it's not like you see on television.

but we turn now to a song- I think this is when the nerves kind of came in, When I was hearing some of the criticism that the judges were giving the performers, because I didn't necessarily believe that I was better than anybody else there after hearing them.

But after hearing what the judges were saying about them, I wasn't sure what to think for myself.

♪ They call you Lady Luck ♪ ♪ But there is room for doubt ♪ ♪ At times, you've had a very unlady-like way of running out ♪ ♪ You're on this date with me ♪ - I was nervous for him, you know, but I was hopeful that he'd win or at least place high.

But, of course, I'm biased, you know?

What parent wouldn't want their child to be up there, but I was proud of him.

♪ You might refuse to stay ♪ ♪ And so the best that I can do is pray ♪ [upbeat, jazzy music] [audience cheers] ♪ Luck be a lady tonight ♪ ♪ Luck be a lady tonight ♪ ♪ Luck, if you've ever been a lady to begin with ♪ ♪ Luck be a lady tonight ♪ ♪ Luck let a gentleman see ♪ ♪ How nice a dame you can be ♪ - As soon as the first contestant was done and I heard the judges, I knew the way it was gonna go down the road.

- [Interviewer] Did it make you more nervous?

- Yes, but I thought, you know, I know him and I know how he carries himself and how he carries a tune and after...

The other gentlemen were wonderful.

But like I said, I'm biased.

♪ Luck let a gentleman see ♪ ♪ How nice a dame you can be ♪ ♪ I know the way you've treated other men you've been with ♪ ♪ How about you bein' a lady with me ♪ - Doing that song, "Luck be a Lady," well, that's my song.

I definitely felt like I put on a good show and could have won.

♪ Luck be a lady ♪ ♪ Luck be a lady ♪ ♪ Luck be a lady, tonight ♪ [audience cheers] [Tyler speaks faintly] - Thank you!

[pensive music] - [Fernando] Unfortunately for Tyler Ricker, luck was not his lady that night.

Instead, Chris Patti from Citrus Springs, Florida was crowned the winner of the 2023 Frank Sinatra Sing-Off.

[audience cheers] But if there's one thing that Tyler Ricker shares with Sinatra, it's that no-surrender attitude.

Nobody ever makes it outta Hoboken without it.

Shortly after the Sing-Off, we caught up with Tyler performing again, but this time on his home field, the boardwalk in Seaside Heights, New Jersey where he naturally won them over, proving for Tyler and every other singer inspired by Sinatra, all the other guys who gave it their all but came up short in Hoboken, there's more than one place and one way to win.

- [Interviewer] So have you seen Tyler sing here before?

- Oh, many times.

- What do you think of him?

- Excellent.

I close my eyes, I think it was Sinatra.

- Were you were a Sinatra fan?

- Oh, yeah.

I'm 76.

I may look 26, but I'm 76.

- It's not 76.

Really?

- Yeah.

- [Tony] They went by quick.

They went by quick.

- [Interviewer] What do you think Sinatra would think of a young guy like this still singing his music?

- In my mind, and Sinatra was from a different era, I think he would say, "This is great.

It's someone that's going to take my legend and make it better."

And he sounds just like Sinatra.

Like I said, if I close my eyes, it's Frank Sinatra.

[audience cheers] - Tyler has serenaded the Jersey Shore and the Tri-State area with the sounds of Frank Sinatra and more.

This is his, okay, his third summer performing Broadway Meets the Beach.

This past week, June 22nd, Tyler had the great honor of being invited to compete in Hoboken's annual Frank Sinatra Sing-Off, competing with gentlemen from across the country and as far as Spain.

Tyler's efforts to keep the great- - So I was going out to dinner with some friends to a nice little Italian restaurant called Ebby's which I love.

I'm sitting there with my friends and there's music starts.

I walk around the corner to the front and this booming like Sinatra voice is coming out of this young kid, basically.

I was like, "Oh, my God."

So I couldn't wait till he finished.

And I went up and I introduced myself and I said, "I do these shows called Broadway Meet the Beach.

Would you be interested in doing the shows?"

He said, "Oh, yeah."

So from then on, he's been in every show.

♪ Start spreading the news, I'm leaving today ♪ [swinging, jazzy music] ♪ I want to be a part of it, New York, New York ♪ ♪ These vagabond shoes are longing to stray ♪ - I love it.

I love it.

I mean, to me that's a performer.

That's like, the show must go on.

Even with the Broadway Meet Beach shows, so many crazy things happen that audience doesn't know about.

And we're like, "Look, if you're not in the hospital, you're not dead, you're doing the show."

[chuckles] ♪ I wanna wake up in a city that doesn't sleep ♪ ♪ And find I'm king of the hill, top of the heap ♪ - [Interviewer] What is it about the performer's spirit, whether you're Frank Sinatra or Tyler Ricker or [indistinct] that no matter what happens to you, you get right back up there on the stage and you sing your heart out?

- I know a lot of famous people and they're not famous because of what they have.

They're famous 'cause of what they didn't have.

And if you're asking me for the truth, I really think that has a lot to do with it, because a lot of famous people I know, that seems to be the case.

♪ It's up to you, New York, New York ♪ [swinging, jazzy music continues] [Tyler vocalizing] - He's not a quitter.

I knew he'd get back on the shtick and get back out there singing, because it's what he loves.

It's what he wants.

- [Interviewer] What do you hope for?

- Well, I don't know if it's his dream, but it's my dream for him is for him to be in a supper club with a big band behind him.

And I just hope to go along the journey with him.

♪ These little town blues ♪ ♪ All melted away ♪ - Singing is always gonna be what I love to do.

I make jokes with people that it's the only thing I'm good at.

But I can never see myself not doing this.

But coming back here and performing, it's like, I'll walk down the boardwalk, people will be like, "Hey, Frankie!"

They might not know my name, but they hopefully will soon.

♪ I'm gonna make it baby ♪ - [Interviewer] What do you think Frank Sinatra would think of Tyler Ricker?

- I think he'd say, "Not bad, kid."

♪ New York, New York ♪ ♪ New York ♪ [audience cheers] - [Tyler] Thank you very much!

[gentle, upbeat music] [gentle, upbeat music continues] ♪ We are exactly what you see ♪ ♪ Bulls dance [indistinct] of me ♪ ♪ Still we find our way ♪ ♪ Some come as quickly as they go ♪ [speaker shouts indistinctly]