Singing guitarist

Ryan Shephard

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About Ryan

Rated the #1 singing-guitarist in Chicago across 3 top booking platforms, and brand new to Encore! 600+ events and memories made.
Singing guitarist
Chicago

I have 15+ years of experience and have performed at hundreds of live events across the United States. I specialize in bringing live entertainment to a wide variety of private and public events such as weddings, corporate events, birthday & holiday parties, music venues, bars & restaurants, or anything else that needs the boost of live music either being the center of attention or background ambience. Background: Ryan Shephard is a singer, songwriter, and guitarist from Cincinnati, OH, (Now located in Chicago, IL) with a large repertoire of experience ranging in numerous different genres of music and musical accolades. He’s played in dozens of bands all over the United States, most notably Freak Mythology, with 600+ shows played in his fifteen-plus year career as a professional musician. Ryan's first original project, Freak Mythology, was started in 2012 as an original project and has won multiple national and international awards for their music. In 2018, Ryan began playing in numerous cover acoustic bands that toured hundreds of venues across fourteen states. Ryan now primarily plays in the greater Chicagoland area, as well as Wisconsin, Michigan, Indiana, Iowa, Kentucky, Tennessee, Minnesota and Ohio at all sorts of different private and public events. Note from the artist: I absolutely love playing live music because of the connection we can create through it. Quality is my expertise! Let me give you a night to remember. I offer a standard one-man acoustic set for a starting price of $800, and potential availability for acoustic duo and trio sets! Not sure about booking just yet? Check out my socials to see when I'm playing in the Greater Chicago area and come say hello! Professional Accolades: - Thumbtack Top Pro '21, '22, & '23 - Past clients include Milwaukee Tool, Fresenius Kabi, Ventas Inc, St. Louis Post, and many more - 2 time Nominee for ‘Best Rock Act’ in the Cincinnati Entertainment Awards. ('18 & '19) - 1st place in the Madison Theater Band Challenge 2018, the largest Battle of the Bands style competitions in the Midwest. - UK Rock Blog PRNAV's Album of the Year 2017. - 1st Place in Cincinnati’s Next Big Band Competition 2017. - Featured in numerous films, including the opening scene of award-winning film director Martin Neveu’s short film, “Feeling Station”. - Selected artist to play at Bunbury Music Festival, Jersey Shore Music Festival, OHMSTEAD Music Festival, Rhythm Brew Music & Arts Festival, and many more national and regional music festivals. - Local & national FM radio airplay. - Local, national, & international online radio airplay. - Fifty thousand combined streams on all major music platforms. - Thousands of copies of 'Freak Mythology' sold. Some Press: "Truly stunning varied selection - current and original yet so evocative of years gone by - a true pleasure to have heard it" — 'Donald Strachen on the Radio' - Donald Strachen “For me it is my 2017 Album of the Year and it will take a lot for any band to beat it." — Pete Divine - PRNAV (2017) “Discovering Freak Mythology, a four piece from Cincinnati, is a refreshing breath of Americana-embedded alternative rock and roll." — Charles Frank - The Jamwich Magazine

Ryan
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5 out of 5
2 verified reviews

Ryan's Reviews

From customers:

JS
Josie S
1 year ago, for a Private event in Chicago
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5 out of 5

All I can say is WOW. We are so ecstatic that we hired Ryan for our wedding day entertainment. Not only is he incredibly, incredibly gifted, but he’s also an awesome person to work with. Ryan set up a consultation right away and asked us to prepare a list of songs/artists/genres that we wanted at our event… and boy, did he deliver. The entire process was seamless from start to finish. Ryan was flexible, accommodating, and always quick in communication. If you’re looking for the perfect addition to take your event over the top and blow away your guests, look no further. He’s the real deal.

AG
Asher G
2 years ago, for a Corporate event in Chicago
Full starFull starFull starFull starFull star
5 out of 5

Ryan was an amazing find! We hired him to play at our company party, and upon first contact, he was so responsive and easy to work with. He showed up with his equipment and guitar, set up quickly, and immediately entertained our crowd of 50. His talent was impressive, as was his repertoire of genres and decades. I would highly recommend him!!

Encore badges
1st Anniversary
This act has been working with Encore for over a year

Ryan's Song list

ALABAMA SHAKES ALWAYS ALRIGHT
ALABAMA SHAKES HOLD ON
ALLMAN BROTHERS BAND RAMBLIN' MAN
ALLMAN BROTHERS BAND BLUE SKY
ALLMAN BROTHERS BAND MIDNIGHT RIDER
AVICII WAKE ME UP
BILL WITHERS AIN'T NO SUNSHINE
BILL WITHERS LOVELY DAY
BILL WITHERS USE ME
BILLY JOEL VIENNA
BILLY JOEL PIANO MAN
BLIND MELON NO RAIN
BOB DYLAN YOU AIN'T GOIN' NOWHERE
BOB DYLAN TANGLED UP IN BLUE
BOB DYLAN MR. TAMBOURINE MAN
BOB DYLAN BLOWIN' IN THE WIND
BOB DYLAN DON'T THINK TWICE, IT'S ALL RIGHT
BOB DYLAN LIKE A ROLLING STONE
BOB DYLAN KNOCKIN' ON HEAVEN'S DOOR
BOB DYLAN THE TIMES THEY ARE A-CHANGIN'
BOB MARLEY IS THIS LOVE
BOB MARLEY THREE LITTLE BIRDS
BOB MARLEY COULD YOU BE LOVED
BRUNO MARS THE LAZY SONG
CHAMPAGNE SUPERNOVA OASIS
CHUCK BERRY JOHNNY B. GOODE
COLDPLAY YELLOW
COLDPLAY VIVA LA VIDA
CRACKER GET OFF THIS
CREEDENCE CLEARWATER REVIVAL PROUD MARY
CREEDENCE CLEARWATER REVIVAL BAD MOON RISING
CREEDENCE CLEARWATER REVIVAL WHO'LL STOP THE RAIN?
CREEDENCE CLEARWATER REVIVAL HAVE YOU EVER SEEN THE RAIN?
DOLLY PARTON JOLENE
EAGLES TAKE IT EASY
EAGLES HOTEL CALIFORNIA
EDDIE VEDDER SOCIETY
ELVIS PRESLEY CAN'T HELP FALLING IN LOVE
ELVIS PRESLEY HOUND DOG
ELVIS PRESLEY BURNING LOVE
ERIC CLAPTON LAYLA
ERIC CLAPTON COCAINE
ERIC CLAPTON LAY DOWN SALLY
FACES OOH LA LA
FLEETWOOD MAC RHIANNON
FLEETWOOD MAC DREAMS
FRANK SINATRA FLY ME TO THE MOON
GEORGE EZRA BUDAPEST
GNARLS BARKLEY CRAZY
GRATEFUL DEAD FRIEND OF THE DEVIL
GRATEFUL DEAD RIPPLE
GRATEFUL DEAD BROKEDOWN PALACE
GRATEFUL DEAD TRUCKIN'
GRATEFUL DEAD FRANKLIN'S TOWER
GRATEFUL DEAD THEY LOVE EACH OTHER
GRATEFUL DEAD DEAL
GRATEFUL DEAD HE'S GONE
GRATEFUL DEAD JACK STRAW
GRATEFUL DEAD BROWN EYED WOMEN
GRATEFUL DEAD SCARLET BEGONIAS
GRATEFUL DEAD FIRE ON THE MOUNTAIN
GRATEFUL DEAD ALTHEA
GRATEFUL DEAD BERTHA
GRATEFUL DEAD MAMA TRIED
GRATEFUL DEAD ME & MY UNCLE
GRATEFUL DEAD NOT FADE AWAY
GRATEFUL DEAD GOIN' DOWN THE ROAD FEELIN' BAD
GRATEFUL DEAD TOUCH OF GREY
GRATEFUL DEAD BLACK MUDDY RIVER
GRATEFUL DEAD DARK HOLLOW
GRATEFUL DEAD GOOD LOVIN'
GRATEFUL DEAD TERRAPIN STATION (LADY WITH A FAN)
GRATEFUL DEAD EYES OF THE WORLD
GRATEFUL DEAD DIRE WOLF
GRATEFUL DEAD NEW SPEEDWAY BOOGIE
HALL & OATES YOU MAKE MY DREAMS (COME TRUE)
HOUNDMOUTH SEDONA
JASON MRAZ I'M YOURS
JEFF BUCKLEY HALLELUJAH
JEFF TWEEDY GUESS AGAIN
JERRY GARCIA BAND MY SISTERS AND BROTHERS
JIMI HENDRIX HEY JOE
JIMI HENDRIX ALL ALONG THE WATCHTOWER
JIMI HENDRIX PURPLE HAZE
JOHN DENVER TAKE ME HOME, COUNTRY ROADS
JOHN LENNON IMAGINE
JOHN MAYER WHO SAYS
JOHN MAYER WAITING ON THE WORLD TO CHANGE
JOHN MAYER I DON'T TRUST MYSELF (WITH LOVING YOU)
JOHN MAYER THE HEART OF LIFE
JOHN MAYER STOP THIS TRAIN
JOHN MAYER LOVE ON THE WEEKEND
JOHN MAYER NEW LIGHT
JOHN MAYER WILD BLUE
JOHN MAYER NEON
JOHN PRINE ANGEL FROM MONTGOMERY
JOURNEY FAITHFULLY
KINGS OF LEON USE SOMEBODY
LED ZEPPELIN GOING TO CALIFORNIA
LED ZEPPELIN D'YER MAK'ER
LORD HURON THE NIGHT WE MET
LYNYRD SKYNYRD SIMPLE MAN
LYNYRD SKYNYRD CALL ME THE BREEZE
LYNYRD SKYNYRD SWEET HOME ALABAMA
MARCY PLAYGROUND SEX & CANDY
MATT DUNCAN EVERLONG
MATT DUNCAN THE KEYS
MUMFORD & SONS I WILL WAIT
MUMFORD & SONS LITTLE LION MAN
NEIL YOUNG HARVEST MOON
NICKELBACK ROCKSTAR
NIRVANA LITHIUM
OASIS THE IMPORTANCE OF BEING IDLE
OASIS WONDERWALL
OASIS DON'T LOOK BACK IN ANGER
OLD CROW MEDICINE SHOW WAGON WHEEL
PAUL SIMON ME AND JULIO DOWN BY THE SCHOOLYARD
PINEGROVE OLD FRIENDS
PINK FLOYD TIME
PINK FLOYD MONEY
PIXIES WHERE IS MY MIND?
PLAIN WHITE T'S HEY THERE DELILAH
PURE PRAIRIE LEAGUE AMIE
R.E.M. THE ONE I LOVE
R.E.M. LOSING MY RELIGION
RADIOHEAD FAKE PLASTIC TREES
RADIOHEAD NO SURPRISES
RADIOHEAD CREEP
SIMON & GARFUNKEL MRS. ROBINSON
SLIGHTLY STOPPID CLOSER TO THE SUN
STEALERS WHEEL STUCK IN THE MIDDLE WITH YOU
STEVE MILLER BAND THE JOKER
STEVEIE WONDER SUPERSTITION
STEVIE RAY VAUGHAN PRIDE & JOY
SUBLIME SCARLET BEGONIAS
SUBLIME BADFISH
SUBLIME WHAT I GOT
SUBLIME SANTERIA
SUBLIME CARESS ME DOWN
SUBLIME GARDEN GROVE
TALKING HEADS TAKE ME TO THE RIVER
TALKING HEADS PSYCHO KILLER
THE ALL-AMERICAN REJECTS DIRTY LITTLE SECRET
THE ALL-AMERICAN REJECTS MOVE ALONG
THE AVETT BROTHERS MURDER IN THE CITY
THE BAND THE NIGHT THEY DROVE OLD DIXIE DOWN
THE BAND I SHALL BE RELEASED
THE BAND THE WEIGHT
THE BEATLES MAXWELL'S SILVER HAMMER
THE BEATLES OCTOPUS'S GARDEN
THE BEATLES HERE COMES THE SUN
THE BEATLES YOU'VE GOT TO HIDE YOUR LOVE AWAY
THE BEATLES YESTERDAY
THE BEATLES NORWEGIAN WOOD
THE BEATLES NOWHERE MAN
THE BEATLES WHILE MY GUITAR GENTLY WEEPS
THE BEATLES HEY JUDE
THE BLACK KEYS LONELY BOY
THE BLACK KEYS GOLD ON THE CEILING
THE BLACK KEYS LITTLE BLACK SUBMARINES
THE DECEMBERISTS DOWN BY THE WATER
THE KINKS LOLA
THE LUMINEERS CLEOPATRA
THE LUMINEERS CLASSY GIRLS
THE LUMINEERS HO HEY
THE LUMINEERS OPHELIA
THE MARSHALL TUCKER BAND CAN'T YOU SEE
THE ROLLING STONES SWEET VIRGINIA
THE ROLLING STONES YOU CAN'T ALWAYS GET WHAT YOU WANT
THE ROLLING STONES WILD HORSES
THE ROLLING STONES BEAST OF BURDEN
THE ROLLING STONES DEAD FLOWERS
TOM PETTY YOU DON'T KNOW HOW IT FEELS
TOM PETTY AND THE HEARTBREAKERS AMERICAN GIRL
TOM PETTY AND THE HEARTBREAKERS I WON'T BACK DOWN
TOM PETTY AND THE HEARTBREAKERS LEARNING TO FLY
TOM PETTY AND THE HEARTBREAKERS MARY JANE'S LAST DANCE
TYLER CHILDERS ALL YOUR'N
TYLER CHILDERS WHITEHOUSE ROAD
TYLER CHILDERS SHAKE THE FROST
TYLER CHILDERS LADY MAY
TYLER CHILDERS NOSE ON THE GRINDSTONE
U2 ONE
VAN MORRISON BROWN EYED GIRL
VIOLENT FEMMES AMERICAN MUSIC
VIOLENT FEMMES BLISTER IN THE SUN
WEEZER SAY IT AIN'T SO
WILCO CALIFORNIA STARS
WILCO HANDSHAKE DRUGS
WILCO IMPOSSIBLE GERMANY
WILCO ONE SUNDAY MORNING
WILCO I AM TRYING TO BREAK YOU HEART
WILCO JESUS, ETC.
YOUNG THE GIANT COUCH SYRUP
ZAC BROWN BAND TOES
ZAC BROWN BAND CHICKEN FRIED

Ryan's Prices

Last updated: 2024

Note: prices may vary based on travel distance. For an exact quote, click “Check availability”.

Standard Prices
DurationPrice
Short performance (up to 15 min)£625
Up to 1 hour£1000
Up to 2 hours£1250
Up to 3 hours£1562.50
Customer questions

What do your clients love most about your performances?

My clients always tell me they love how I'm able to get the crowd going, and how communicative I am. I truly pride myself in being as professional as I possibly can for all of my clients.

Which venues have you performed at in the past?

Madison Theatre Bogarts Reggie's Chicago Willis Tower Rivers Edge Amphitheatre

Which artists have you been most influenced by?

The Beatles, The Rolling Stones, Grateful Dead, and Led Zeppelin!

What is the most high profile gig you've performed?

I have played many high profile gigs, but the one that is likely the most notable was playing at the home of one of a Fortune-500 CEO in the United States! I have also played for actors, prominent business owners, and politicians.

What if my timings change after I've booked you?

I will always try my best to work with you, but if I am booked on another date, I will not be able to be able to accommodate your event.

Can you provide an iPod/DJ service before and between your sets?

Yes! I'll always provide a playlist of music for any event I am hired for during breaks.

How much time do you need to set up?

I typically only need between 10-20 minutes to set up my equipment depending on the venue. If the event is in a highrise building or is difficult to access, I may need more time.

Can I pick the songs you play from the set list?

Every show I play I will attempt to curate to my client's preferences. I have a list of over 250 songs to choose from, and after we move forward with booking, I even offer a hub for clients to request songs in advance!

Do you bring all the equipment you need to perform?

I provide 100% of the equipment needed to perform, outside of a power source!

Can you learn song requests before the event?

Absolutely! If you have a special song you'd like to hear, just let me know and I will do my best to make it happen.
Musicianship
Genres:
Classic rock, Christmas, Traditional church music, Contemporary classical, Folk, Bluegrass, Country, Folk rock, Jazz, Blues, Light music, Easy listening, Originals, Pop, Acoustic, Ambient pop, Americana, Covers, Funk, R&B, Soul, Top 40, Tribute, Vintage, Rock, Alternative rock, Britpop, Indie, Pop rock, Rock 'n' Roll
See all genres
Instruments:
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Event types:
Private event, Wedding, Virtual event, Wedding proposal, Funeral / Memorial service, Hotel / Restaurant event, Bar / Club / Venue event, Corporate event, Charity event, Concert, Recording session, Cruise, Birthday party, Christmas party, New Year's Eve
See all event types
Other skills:
Lyricist, Arranger, Songwriter, Live looping, Instrumental teaching
See all skills