Vanessa Carlton at City Winery.

An Evening With Vanessa Carlton: Veils Tour

$67.20 – $91.20
May 2 @ 7:30 pm
|Recurring Event (See all)

Vanessa Carlton continues to expand creatively as an artist as seen in her upcoming seventh studio album Veils produced by Dave Fridmann (MGMT, Flaming Lips) to be released early 2026. Fridmann also produced her last album Love is An Art (2020). Through her songs, Vanessa invites listeners to explore the Veils in their own lives. […]

Rakim at City Winery.

Rakim

$78
May 3 @ 5:00 pm

In the history of the Hip-Hop, few artists have had as great an impact on the development and progression of the art forms lyrical style as Rakim Allah. Universally referenced as one of the Masters of the Microphone and an influence and inspiration to his peers and followers alike, Rakim first exploded onto the scene […]

Rakim at City Winery.

Rakim

$78
May 3 @ 8:30 pm

In the history of the Hip-Hop, few artists have had as great an impact on the development and progression of the art forms lyrical style as Rakim Allah. Universally referenced as one of the Masters of the Microphone and an influence and inspiration to his peers and followers alike, Rakim first exploded onto the scene […]

Mom’s Night Out with The Mama’s Den at City Winery.

Mom’s Night Out with The Mama’s Den

$42
May 6 @ 7:30 pm

Mother’s Day is one day… but motherhood deserves a whole month (if not MORE). This May, the award-winning The Mama’s Den podcast is bringing the sisterhood off the mic and into the room for the Mom’s Night Out Tour — a Motherhood Month celebration at City Winery! Join the hosts of the beloved podcast for […]

Heated Rivalry Trivia at City Winery.

Heated Rivalry Trivia

May 7 @ 7:00 pm

Lace up and step onto the ice, because we’re diving headfirst into insults that turn into longing looks, enemies who refuse to stop orbiting each other, and a rivalry so intense it accidentally becomes a love story. Andrew Genius hosts Heated Rivalry Trivia at City Winery on May 7 at 7pm, with questions covering Game […]

Eric Bellinger at City Winery.

Eric Bellinger

$54
May 8 @ 7:30 pm

Eric Bellinger’s journey has been a remarkable evolution from the streets of Compton to becoming an international sensation, marked by his Grammy-winning artistry and prolific songwriting skills. Hailing from a musical lineage as the grandson of Bobby Day, a hit songwriter for the Jackson 5, Eric faced the pivotal decision of pursuing a career in […]

Aida Ade at City Winery.

Aida Ade

$30
May 9 @ 7:30 pm - 9:30 pm

Aida Ade is an eclectic soul artist from St. Louis whose music blends soulful storytelling, experimental sound, and emotional honesty. Drawing from a wide range of influences, Aida Ade crafts songs that move fluidly between genres while remaining rooted in the rich feeling and authenticity of soul music. In 2025, Aida Ade released her debut […]

David Broza at City Winery.

David Broza

$78 – $102
May 10 @ 7:00 pm

David Broza is an internationally renowned Israeli singer-songwriter, recognized for his dynamic guitar performances and humanitarian efforts. His signature sound brings together songs in Hebrew, Spanish and English, with the influence of Spanish flamenco, American folk, rock and roll, jazz and poetry. Social justice and peace advocacy are embedded in Broza’s work, as his 1977 […]

LYLE LOVETT at City Winery.

Lyle Lovett Up Close: Songs & Stories

$162
May 13 @ 7:30 pm
|Recurring Event (See all)

A singer, composer and actor, Lyle Lovett has broadened the definition of American music in a career that spans 14 albums. Coupled with his gift for storytelling, the Texas-based musician fuses elements of country, swing, jazz, folk, gospel and blues in a convention-defying manner that breaks down barriers. Lovett’s live performances show not only the […]

LYLE LOVETT at City Winery.

Lyle Lovett Up Close: Songs & Stories

$162
May 14 @ 7:30 pm
|Recurring Event (See all)

A singer, composer and actor, Lyle Lovett has broadened the definition of American music in a career that spans 14 albums. Coupled with his gift for storytelling, the Texas-based musician fuses elements of country, swing, jazz, folk, gospel and blues in a convention-defying manner that breaks down barriers. Lovett’s live performances show not only the […]

LYLE LOVETT at City Winery.

Lyle Lovett Up Close: Songs & Stories

$162
May 15 @ 7:30 pm
|Recurring Event (See all)

A singer, composer and actor, Lyle Lovett has broadened the definition of American music in a career that spans 14 albums. Coupled with his gift for storytelling, the Texas-based musician fuses elements of country, swing, jazz, folk, gospel and blues in a convention-defying manner that breaks down barriers. Lovett’s live performances show not only the […]

Sip N'Serve Drag Brunch: Sunkissed! at City Winery.

Sip N’Serve Drag Brunch: Sunkissed!

May 16 @ 12:00 pm

Get ready to soak up the glam at City Winery’s drag brunch, SUN-KISSED, featuring Moxie Contin & Friends! Sip, savor, and bask in a sun-soaked celebration of high-energy performances, vibrant looks, and unforgettable vibes. Moxie will guide you through a brunch full of laughs, lip-syncs, and sunny surprises that’ll leave you glowing. Don’t miss your […]

Infinite 80s at City Winery.

Infinite 80s

$36
May 16 @ 7:30 pm

Step into the dreamworld of the 1980s—where eyeliner ran deep, synths shimmered, and guitars wept with emotion. INFINITE 80s is your portal to the post-punk, new wave, and alt-pop legends who defined a generation and reshaped our lives. Celebrating the music of The Cure, The Smiths, Depeche Mode, U2, Talking Heads, Violent Femmes, New Order, […]

Soul Brunch at City Winery.

Soul Brunch: Tribute to Gap Band and Charlie Wilson

May 17 @ 12:00 pm

Get ready to groove as PureSoul presents the ultimate Charlie Wilson and The Gap Band tribute, celebrating timeless hits like “Outstanding”, “Burn Rubber on Me”, “Can’t Live Without You” and more. Experience electrifying performances that bring Wilson’s smooth vocals and The Gap Band’s funk-driven energy to life. Sing along to classics like You Dropped a […]

Darius Bradford at City Winery.

Darius Bradford

$48 – $54
May 17 @ 7:00 pm

Darius Bradford has been boldly representing St. Louis on the comedy standup scene locally and nationally for over than 25 years. He’s made a name for himself over the years from opening for Steve Harvey, Cedric The Entertainer, D.L. Hughley, and the late great Bernie Mac on their legendary “The Original Kings of Comedy Tour”, […]

Tangerine: Tribute to Led Zeppelin at City Winery.

Tangerine: Tribute to Led Zeppelin

$30
May 20 @ 7:30 pm

Tangerine: A Tribute to Led Zeppelin brings the timeless power, soul, and mystique of one of rock’s greatest bands to the stage in an unforgettable live experience. Led by the dynamic Jason Nelson Band, this electrifying tribute captures the spirit and sound of Led Zeppelin with passion, precision, and reverence. From the thunderous riffs of […]

Ode to Neo Soul at City Winery.

Ode to Neo Soul

$42 – $54
May 21 @ 7:30 pm

An intimate, soul-stirring concert experience paying tribute to the evolution of soul music — from classic roots to the smooth, conscious sound of Neo Soul. Ode to Neo Soul blends rich vocals, heartfelt storytelling, and timeless grooves inspired by the artists who shaped a generation of soulful expression. Expect powerful performances, deep emotion, and a […]

Murphy Lee and Kyjuan at City Winery.

Murphy Lee and Kyjuan of the St. Lunatics

$54 – $78
May 22 @ 7:30 pm

“Where Hip Hop meets R&B meets Comedy” Experience Hip-Hop trailblazers and Grammy Award winner, Murphy Lee & Kyjuan of the legendary “St. Lunatics” with a live band ensemble in a one-of-a-kind special night of music, laughs, and smooth intentional vibes that only the St. Lunatics can provide.

George Lopez at City Winery.

George Lopez

$54 – $78
May 23 @ 8:30 pm
|Recurring Event (See all)

George Lopez’s illustrious and multi-faceted career encompasses television, film, stand- up comedy, and late-night television. Lopez has broken ground for Latino comics by embracing his ethnicity, confronting racial stereotypes, and fighting for his community on and off the stage. Lopez stars in and executive produces his multi-camera comedy series for NBC, Lopez vs Lopez, featuring […]

George Lopez at City Winery.

George Lopez

$54 – $78
May 24 @ 5:00 pm
|Recurring Event (See all)

George Lopez’s illustrious and multi-faceted career encompasses television, film, stand- up comedy, and late-night television. Lopez has broken ground for Latino comics by embracing his ethnicity, confronting racial stereotypes, and fighting for his community on and off the stage. Lopez stars in and executive produces his multi-camera comedy series for NBC, Lopez vs Lopez, featuring […]