Wilmington's inner-city Sinatra singer just landed on national TV. He couldn't care less.

Ryan Cormier
Delaware News Journal

One thing is not up for debate: There's only one Sean Reilly.

And it's not just because he's Wilmington's gay, inner-city Irish Catholic Frank Sinatra singer.

A dozen years ago, at 52, he entered the "Sinatra Idol" contest in Sinatra's hometown of Hoboken, New Jersey, and won. That's when the job recruiter started a new chapter in his overflowing book of life.

"And I'm nothing like Frank. I don't even drink!" he jokes, exposing his oversized personality. "People say, 'You're Frank Sinatra and you don't drink?' I say, 'Even worse, I'm Irish and I don't drink.' I'm more ashamed of that than anything."

For nearly four decades, Reilly has run his life from what he calls the captain's seat in his historic Federal-style home at West and Fourth streets, soaking in both the city's past and present.

Sean Reilly works from his Quaker Hill home as a corporate recruiter, also performing as a Frank Sinatra entertainer.

Dressed in a blue checkered shirt and blue jeans, which help make his twinkling blue eyes dance, Reilly thrives in the diverse Quaker Hill neighborhood where he stands out a bit, especially when he strolls down Fourth Street in his tuxedo walking to his downtown gigs.

Where the past and future meet

Reilly was born into Brandywine Hundred suburbia as a "gay man trapped in a straight man's body," as he puts it. Once he left, he never looked back, drawn to the bustling energy of the city, even when he sees a car crash or sex act right outside his window. (Neither is all that uncommon.)

Built in the early 1740s, his home is across from the historic Wilmington Friends Meeting House, which is also the burial site of Delaware Underground Railroad stationmaster Thomas Garrett, a friend of Harriet Tubman, who is credited with helping nearly 3,000 slaves reach freedom.

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Given that one of Wilmington's founding fathers, William Shipley, gave the land for the meeting house, it should come as no surprise that Reilly ended up as the owner of the nearby Shipley Grill (and the ROAM nightclub above it) from 1989 to 2001.

It's also not surprising that he knows all the details about George Washington’s time in Wilmington, when he was headquartered here in August 1777.

Wilmington's Sean Reilly, a Frank Sinatra impersonator, performs on "Full Frontal with Samantha Bee" in late March. The segment was filmed in Atlantic City, N.J.

It's easy to tell that the self-described "Delaware fanatic" has actually read the piles of Wilmington and Delaware history books that can be found throughout his 25-window home on a hill that offers views of downtown Wilmington and the Delaware River.

He's a man living in two worlds at once, past and present. And that's the way he likes it.

"[Henry David] Thoreau said one of the greatest things I've heard in my life: The meeting of two eternities, the past and the future, is precisely the present," Reilly said.

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And that's the way he feels about listening to Sinatra and the standards that the Chairman of the Board brought to life.

"If you put on some old Sinatra, you can almost go there because your mind is the traveler. You don't have to go anywhere," said Reilly, whose facial features bare a striking similarity to the real Sinatra, even past the blue eyes.

Wilmington's Sean Reilly will perform at The Queen on June 16 in Wilmington.

Wee small hours

With a dozen years as a Sinatra tribute artist under his belt, Reilly was performing about 180 gigs a year before the pandemic hit, taking stages from New York to Washington, D.C., with much of his work closer to home in recent years.

After singing favorites like "Fly Me to the Moon (In Other Words)" and "You Make Me Feel So Young" at clubs, restaurants and nursing homes across the region for years, he landed on national television in March when he was hired to sing on the Atlantic City boardwalk for a segment on TBS' "Full Frontal with Samantha Bee."

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There he was fully dressed in his tuxedo belting out a tune on national television, something his mother could probably never imagine years ago. She was the one who would sing Sinatra's "In the Wee Small Hours" to him at night instead of children's lullabies.

"In the wee small hours of the morning/While the whole wide world is fast asleep/You lie awake and think about the girl/And never, ever think of counting sheep," he sings to an audience of one during a recent interview. "It was a bug in my ear as an infant."

'I will never be called daddy or Father'

As he got older, Reilly wasn't staying up thinking about girls, however. He knew he liked guys. And as a Salesianum School student in the early 1970s from a religious family, it meant coming to terms internally that his dream of being a priest was dead.

He also didn't want to play sports like his brother Kevin, who went on to have a short career with the Philadelphia Eagles whose arm was later amputated due to cancer.

"I can't do s--t. I'm a f--king prisoner," Reilly remembers thinking as a teenager, unable to reveal his true self to his family.

While he firmly believes he was meant for the life he's living now, he still can't shake the thought of missed opportunities due to being gay, things that were denied him by society (and from within) at the time.

And those feelings cover both his personal life and professional dreams in the church.

Sean Reilly brings his Frank Sinatra show to The Queen's Knight's Bar on June 16.

"I will never be called daddy or Father because I can't be either. Both is what I prefer to be than what I am," he said, bluntly explaining the sacrifices he said he had to make.

"I hate what I am. I hate this. But I'm relegated to it now because I belong in this purpose right now. It gets complicated when you think about what you should have been and what you could have been," he continued. "My brother was on the Eagles. My grandfather was a state senator. My father had the best liquor store [Van's Liquors on Concord Pike] in the state.

"I couldn't do anything to make too much of a noise. I didn't want to disturb their worlds."

Finding love

Everything changed when he met Anthony Mombro, a strikingly handsome 20-year-old DJ with blue eyes and blonde hair at a Wilmington after-hours club called Danceland. It was four blocks from where Reilly now lives at would later become his Shipley Grill and ROAM.

It was January 1978 and Reilly was 21. (As the 1996 cover of Delaware Today magazine attests, Reilly isn't bad looking either, named one of the state's "sexiest singles" alongside Dogfish Head founder Sam Calagione that year.)

Sean Reilly (left) with his late partner Anthony Mombro.

Mombro was out and fearless, so Reilly held on tight and began to break from his cocoon. And that's something he will never forget — the moment he began to transform into his true self. He still lives by Mombro's mantra to this day: Don't ever be afraid to be who you are.

They immediately fell in love and that Valentine's Day, Mombro gave him two greeting cards, which he kept under his mattress to hide from his family.

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One night, after telling his parents, Francis and Katherine, he was going to see a girl, his sisters went into his room to watch television and broke his bed while playing around. As his father put the bed back together, the cards fell out along with his secret.

He told his parents that the cards "are as they seem to be" and let's just say it did not go well. After a couple of months living in the house with his secret exposed, he and Mombro left everything they knew behind and drove to Atlantic City in his black 1964 Chevrolet Corvair. If it kind of sounds kind of like a gay Bruce Springsteen song, you'd be right.

Little did he know, he'd be back in the same oceanside New Jersey town four decades later filming his "Full Frontal" television segment for a worldwide audience.

He couldn't help but think of Mombro when he made that same drive earlier this year for the TV taping. Mombro, the forever love of his life, died in 2000 at 42 of complications from AIDS.

Mounted pages from a 1996 edition of Delaware Today that featured Sean Reilly on the cover as one of the state's sexiest people.

They had been inseparable for 22 years.

"Nothing has ever come close since. You just can't top it," he said of his partner, whose framed photo sits on a ledge above his kitchen sink.

Their brief escape to Atlantic City allowed the family situation back home to calm down and soon he was back working at his father's liquor store. This time, his family knew who he was, but the issue was left unspoken and hidden with Mombro excluded from family events.

It was when Reilly told his mother that Mombro had AIDS and she grabbed her son's hand, taking the opportunity to come closer. And then she bonded with Mombro.

As Reilly put it, "Know that song that goes, 'I want a girl, just like the girl that married dear old Dad'? That's what Anthony was. He was my mother! Those two were the same animal."

At one party, he watched in amazement as Mombro and his mother sat together in a corner and talked for four hours. For three years before Mombro died, his two worlds were finally intertwined.

Frank Sinatra tribute artist Sean Reilly looks for photos of him performing in his home in Wilmington Tuesday, May 4, 2021.

"And it was better late than never. Better to loved and lost. All of those things," he said. "But again, it made me what I am today."

His parents, now both in their 90s, will celebrate their 71st anniversary later this month.

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It's his Sinatra singing that led to his father saying four words every son wants to hear from their dad at least once in their lives: "I'm proud of you."

It came after a performance in a church basement, of all places.

"First time in my life he said that," Reilly said. "He's a good, decent, honest, caring and loving man. I thought, 'Wow. OK. I guess I did it right.'"

'Common denominator finder'

As COIVD-19 restrictions relax, Reilly is now back in his tuxedo and on stage. 

Sean Reilly’s tribute to Frank Sinatra comes to The Queen in Wilmington on June 16.

He will perform at The Queen's Knights Bar (500 N. Market St., Wilmington) on June 16.

This fall, he'll put on a show unlike he has ever done before. The Queen's upstairs Crown Room will be transformed into a 1940s-era supper club on Oct. 1 with Reilly on stage, a "dressed to impress" crowd in the seats and a three-course meal on the menu.

Reilly will be doing what he does best: bringing the past to life, telling the stories behind the songs before belting them out backed by a trio. This time it won't just be Sinatra tunes, but "songs of the great American songbook." (Tickets will be available at thequeenwilmington.com.)

This is what he gets excited for. What does he not get excited for? Landing on "Full Frontal" with an audience of millions.

His name wasn't used on the broadcast, so it didn't mean a jump in business, although a few old friends saw it and reached out. But things like that don't excite Reilly. 

Sean Reilly's trophy from winning the 2009 Sinatra Idol Contest.

It's the music and connecting with people, just like he saw Sinatra do at The Spectrum when he made the 20,000-person arena feel like an intimate club. Reilly's performances can really change someone's day, usually happening at the least glamorous of gigs, like playing nursing homes.

"Someone's head will lift during a song and the nurse will tell me it's the first time she looked up in 10 years," said Reilly, whose drive to help others is fueled by his faith.

Now 64, his long and sometimes complicated path has led him to spend his time on stage. And he absolutely loves it.

"It keeps me moving. I see people I would have never met and go places I would never have gone. And I have the privilege of bringing music to people, the soundtrack of their lives," he said.

Frank Sinatra tribute artist Sean Reilly has Sinatra memorabilia all over his home in Wilmington.

When he's not singing or talking about history, he's cracking one liners and dropping into impressions that range from Jerry Lewis to Rodney Dangerfield. He is, after all, an entertainer now.

And if you ask him about what it's like being a gay Sinatra singer, performing to some crowds that may not be as open-minded as others, the humor spills out with a message behind it — a message that seems especially pertinent these days.

"Do you know how many people love Sinatra and hate f----ts? A lot! But I'm doing Frank and they don't care," he says. "I'm a common denominator finder. I'm going to find common ground with you and we're going to latch onto that and build."

He's been doing it his whole life. Why stop now?

Have a story idea? Contact Ryan Cormier of The News Journal at rcormier@delawareonline.com or (302) 324-2863. Follow him on Facebook (@ryancormierdelawareonline) and Twitter (@ryancormier).