Stephen Triffitt as Ol’ Blue Eyes

WHEN a young Frank Sinatra worked as a waiter at a New Jersey roadhouse, the job description had a twist that would change the face of popular music.

As well as serve tables, he had to sing while he was doing so. The diner was connected to a popular radio station – hence the need for singing waiters – and Frank was quickly spotted. The rest, as they say, is history.

And how Stephen Triffitt, recognised today as the world’s number one singer of Ol’ Blue Eyes’ back catalogue, got the gig would echo with the man he emulates.

On Sunday (June 11), Stephen is appearing for one night only in the historic surroundings of Cadogan Hall. Joined by the Manhattan Swing Orchestra – a full ensemble – he will be performing the seminal 1956 hit album, Songs For Swingin’ Lovers, which gave the world such classics as I’ve Got You Under My Skin and You Make Me Feel So Young.

“I have been listening to him and singing along since I was 15,” says Stephen.

Working in Tenerife three decades ago kick started a new career. “I went into a bar and sung one of his songs,” he recalls. “People thought it sounded good – so I sang a few more.”
On his return to England, he had the confidence to do Frank turns whenever he could.

“People said ‘you sound like him’. I suppose unconsciously I was trying to, as I’d sung along so many times,” he adds.

Then came a big break. He was selected for the TV show Stars In Their Eyes and came runner up in the final. The make-up and costume crew transformed him into Frank and, as well as the voice, he looked in the mirror and saw Frank staring back. That was 23 years ago – and the experience set him up.

“I’d practise and practise – I’d sing Frank songs as I took my kids to school. They got to know the music as well as I did – and would correct me when I got something wrong,” he says. “They were as excited as I was to go on the show. The actual day was absolutely terrifying. At the time, I was so green, and I had never actually tried to turn into Frank physically.”

Stephen Triffitt performs as Frank Sinatra: ‘I have been listening to him and singing along since I was 15’

From his TV success, Stephen earned a role singing in a West End show called No Way Out. “It had Bob Geldof’s other half in it and he was in the audience,” recalls Stephen. “I performed the opening song – Cheek to Cheek – and then at the end, I sang another.

“I got talking to Bob that night afterwards and someone took our picture and put it in OK magazine.”

This photo sparked a Transatlantic opportunity.

“A producer in America saw the photo,” he says. “She had been looking the right person to play Frank in a Rat Pack show.”

He scooped a job out of the blue, working in Atlantic City and then did a three-month stint in the exacting environment of Las Vegas, a place full of Sinatra devotees and with a special link to the performer.

“I had to really study Frank, really get every mannerism,” he recalls. “I was given hundreds of films and footage to watch. They said to me – ‘here you go, get that right’. I’m originally from Bradford and, funnily enough, there were similarities and it gave me a start on doing Frank’s accent.”

Growing up in a Forces family, he travelled around the world as a child, and that also helped him develop an ear for accents, he says.

Stephen’s uncanny ability to bring the star back to life has seen him perform on CNN and CBS in the US, and both ITV and BBC closer to home. Both Simon Cowell and Bob Geldof booked him to play at their birthday parties, and he has hosted sell out shows in the West End.

There is an enduring beauty in Sinatra’s music, he says, that still enchants and charms. And Songs For Swingin’ Lovers was an important milestone in the singer’s career. In his early days, he had recorded classics for Columbia and this was a departure from what his public knew.

He moved to Capitol Records in the 1950s and caught the jazzier, swing style of the period at the perfect time. “He sounded so smooth, so sweet – it was like velvet, and the songs on that album helped define him and shape hm for the rest of his career,” says Stephen.

For Stephen, Frank’s tone and timing is endlessly fascinating. “He could play about with the arrangements, extend phrasing,” he says. “It was a period when his work was described as woody, smokey, atmospheric.

“I try to sing the songs as closely as possible to the style on the album – and I’ll tell the story behind each song, too.”

• Frank Sinatra’s Songs for Swingin’ Lovers! Stephen Triffitt as Frank Sinatra, featuring the Manhattan Swing Orchestra.
Sunday June 11 2023, 6.30pm
Cadogan Hall, 5 Sloane Terrace, SW1X 9DQ
https://cadoganhall.com/whats-on/songs-for-swingin-lovers-2023