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Jeff Wessman

Top Performer

Oakland, CA

$400 and up

Travels nationwide

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Come Fly With Me

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The Lady is A Tramp (with Nine piece band)

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A Swingin' Affair! - Septet

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Classic Rock '50s - '60s - '70s

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Jeff Wessman with Trio

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Sinatra Solo show

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Bobby Darin Songs

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Sinatra Solo Show with guitar

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Johnny Cash cover

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Sinatra style at Colombo Club

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My Way

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Big Band Finale!

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Sinatra (and more) show with sextet

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My Way

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Big Band!

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Frank Sinatra and Marilyn Monroe - Casino Event

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Big Band

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ASA Quartet

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Quartet

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With Sextet (photo by Tim Ulmer)

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Quintet with guitar

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New Year's Eve

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Headshot

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on the catwalk

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Hollywood Parties love Frank!

Overview

Jeff Wessman captures the sound and style of Frank Sinatra better than anyone! His show, A Swingin' Affair! is a tribute to Frank Sinatra and Friends, with popular songs by Sinatra, Dean Martin, Bobby Darin, Tony Bennett, and others. His versatility as a singer is unparalleled and doesn't stop with crooners. His repertoire includes other classic party favorites by Elvis, Beatles, Elton John, Neil Diamond and more). Jeff brings humor and stage presence to each performance making for a fun and memorable event.

Jeff performs regularly as a soloist or with his live ensembles (from a trio to a full 17-piece big band).

Jeff offers remote Livestream concerts.


Reviews

57 reviews

Small thumbnail image for reviewer Lexi L.

Lexi L.

April 27, 2026

Jeff is the best!

We brought in Jeff to perform at our 99-year-old mother’s backyard birthday party and he truly made it unforgettable! She has a hard time remembering things that happened even 10 minutes ago, but the next day she kept asking if the 'handsome performer' was going to come back - which tells you everything you need to know!!

Jeff was incredibly professional from start to finish. Very quick to respond and incredibly easy to work with. He performed many of her favorite old classics and even went the extra mile to learn a few of her favorite songs from a lesser-known singer from the 50s which made the moment even more special.

We couldn’t have asked for a better experience and will absolutely be booking him again for her 100th celebration!

Hired as: Crooner, Frank Sinatra Impersonator, Oldies Music, One Man Band, Singing Guitarist, Sound-Alike


Small thumbnail image for reviewer E W.

E W.

December 16, 2025

Amazing!

Jeff was very professional and easy to work with. He and his band were a wonderful addition to my party providing that extra something that made the event even more memorable. Jeff is an excellent singer and truly evokes the spirit and style of Frank Sinatra in his appearance and his voice. He has a warm presence and is quite entertaining. I would highly recommend Jeff for any event.

Hired as: Frank Sinatra Impersonator


Small thumbnail image for reviewer Event C.

Event C.

September 3, 2019

Great performance at a Charity Gala!

Jeff and the musicians in his 6 piece band were very professional and put on a great performance at a local charity Gala dinner in the central valley. Jeff charmed the audience completely and had people dancing most of the evening. He was very punctual. Our event schedule was a bit 'flexible' which presented some challenges for his musicians but Jeff always managed to make things work out. His performance received rave reviews from our guests and we recommend him highly.

Hired as: Big Band, Rat Pack Tribute Show, Tribute Artist

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Jeff Wessman

Grazie mille Andrea!


Small thumbnail image for reviewer Marian S.

Marian S.

May 9, 2026
Verified review

Wildly exceeded our expectations !

Jeff provided an over the top performance and nuanced experience at my mother’s 100th birthday party. Mom has always been a huge Sinatra fan and Jeff made it personal with all of her favorites…she was swaying in her chair with tears in her eyes. Jeff, as it turns out, performed at my Mom’s 90th, and we were all thrilled to see him again doing his Sinatra thing in his inimitable style.

Hired as: Impersonator, Oldies Music


Small thumbnail image for reviewer Kathryn D.

Kathryn D.

April 21, 2026
Verified review

Jeff provided a great time.

Jeff is an excellent entertainer, sings beautifully and we all enjoyed his performance immensely!

Hired as: Crooner

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Booking information

Price range: $400 and up

Languages: English

Gig length: 45 - 180 minutes

What to expect

As a professional I am easy to work with. I'm prompt, responsible and communicate well with my clients to ensure that their expectations are not only met but exceeded.

As an entertainer I bring humor, musicality and a spirit of generosity, so that each performance is a success, elevating the event into something truly special and memorable.

As an artist, I know my material (i.e. the songs and the singers) thoroughly, bringing to life the sound and spirit of Sinatra with pitch perfect renditions of the greatest music ever written.

About

Jeff Wessman is a tribute singer based in the San Francisco Bay Area specializing in the music of Frank Sinatra. His tribute to Sinatra and Friends, “A Swingin’ Affair”, is a lively revue of popular songs with remarkable vocal renditions of all the greats including Frank Sinatra, Dean Martin, Tony Bennett, Bobby Darin, Michael Buble’, and Nat King Cole.

With his big band, ensemble, or as a soloist, Jeff appears regularly throughout the San Francisco Bay Area and across the US including such notable venues as the penthouse at the Fairmont in SF, the Colombo Club, and the Cocoanut Grove in Santa Cruz. Jeff has enlivened many life events including those for the Make a Wish Foundation, the Pacific Italian Alliance, On Lok, The Elks, The Rotary Club, and others. His performances have added fun and warmth to scores of weddings, anniversaries, birthdays and holiday parties. With more than 170 performances a year, Jeff is quite in demand.

"A man of a thousand voices" - Jeff also performs the songs of Hank Williams, Johnny Cash, Willie Nelson, Elvis, The Beatles, Neil Diamond, John Denver and many others.

In addition to his music work, Jeff has a media company, Inner Active Media, providing audio, video, livestreaming and online marketing services.

Jeff is based in Oakland CA.

Additional booking notes

If performing solo or with a band, I provide my own sound system. If solo, depending on the size of the event, I require a small table, such as a card table, to set up on. If a large room, and/or with a large audience and potential background noise, I provide a PA system, unless one is available at the venue, in which case I will use the house mic to get a feed from my monitors to the house PA.

When performing solo I sing to high quality tracks to reproduce the big band orchestra. I can also provide a large classy "branded" backdrop to provide more visual interest, as if I weren't enough.

For sets longer than an hour I like to take a short (5 min.) break every 45 minutes or so.

Set list

A more complete song list with over 200 songs can be provided upon request. For those interested in expanded repertoire I also do country and rock classics from the '40s, '50s, '60s and beyond.

Ain't That a Kick in the Head
Best is Yet to Come
Beyond the Sea
Blue Moon
Chicago
Come Fly With Me
Everybody Loves Somebody
Fly Me To the Moon
I Could Have Danced All Night
I Get A Kick Out of You
I Left My Heart in San Francisco
I've Got the World On A String
I've Got You Under My Skin
L-O-V-E
Love is Here To Stay
Luck Be a Lady
Mack the Knife
New York, New York
Night and Day
South of the Border
Steppin' Out With My Baby
Strangers in the Night
Summer Wind
That's Amore'
The Way You Look Tonight
Volare
Where or When
Witchcraft
You're Nobody till Somebody Loves You

Influences and inspiration

Frank Sinatra, Dean Martin, Tony Bennett, Jerry Lewis, and Bobby Darin.

Setup requirements

PA System

Microphone

Mixer