On October 10, 2025, the Monona Terrace Convention Center glowed with energy, rhythm, and gratitude as the Urban League of Greater Madison hosted The Urban Cabaret 2025. A night dedicated to celebrating the tenth anniversary of Dr. Ruben Anthony’s visionary leadership. The evening stood as both a tribute and a testament: a living example of how one leader’s commitment can ignite transformation across an entire community.
Over the past decade, Dr. Anthony has guided the Urban League of Greater Madison through bold expansion and deepened impact. Under his direction, programs that once reached dozens now empower hundreds—helping individuals secure employment, build businesses, and access opportunities once out of reach. His leadership has not only strengthened the League’s foundation but has reignited a sense of hope and unity across Madison’s urban and multicultural communities. This milestone year, the Urban Cabaret returned to Monona Terrace—its home stage—to honor that very legacy.
A Night of Artistry and Empowerment
Emceed by Kayla Conklin, President of the Urban League Young Professionals, the event blended celebration with purpose. Conklin’s charisma and grace set the tone for the evening, weaving the performances and recognitions into a seamless flow of gratitude and joy. From the first moment, the audience could feel that this was more than a fundraiser—it was a cultural experience, a reflection of Madison’s creative pulse.
The stage came alive with performances that mirrored the richness of the city’s diverse talent. Award-winning singer-songwriter Adem Tesfaye filled the room with soulful sounds that fused funk, reggae, blues, and hip-hop into one compelling story after another. Matthew Teague, a world-class magician, brought laughter and wonder through his blend of magic and comedy, reminding attendees that community progress, too, begins with a spark of imagination.
The artistry continued with visual and performing excellence: Tony Catteruccia, the renowned urban artist known for his murals and tattoo artistry, presented his striking visuals as living testimony to the vibrancy of local creativity, including the piece created that very evening! The electric hip-hop crew, led by community activist Clyde Mayberry, electrified the crowd with choreography. There were also performances by Ogunde Tremayne and Alleenah Hancock-Jammeh and Steven Espada Dawson, Madison’s Poet Laureate. Their collective presence reflected the very soul of the Urban League’s mission: to empower through creativity, equity, and community connection.
The night also featured soulful sounds from Timeless, an R&B ensemble led by Leotha and Tamera Stanley, Yancyy, and special guests. Their smooth harmonies brought nostalgia and inspiration, bridging generations and reminding everyone of the power of unity through music. Truly soulful for your ears.
Honoring Excellence and Commitment
Beyond the art and music, The Urban Cabaret 2025 was a platform for recognition—honoring those who continue to push Madison forward. The Whitney M. Young, Jr. Equal Opportunity Awards celebrated Charlestine “Charlie” Daniel and Derrick L. Smith for their lifelong dedication to equity and inclusion. The President’s Awards recognized Shiva Bidar-Sielaff as Community Champion, Korbey White as Rising Star, and Cheryl Wittke as Community Collaborator. Each honoree stood as proof that progress is not built overnight—it’s built together, with hands that serve and hearts that believe.
The event also spotlighted local educator and filmmaker Dr. Charles Taylor, whose work in racial equity, education, and cultural understanding has made a lasting impact across Wisconsin. His recognition underscored a key message of the evening: leadership takes many forms, and each act of service contributes to the larger movement for justice and empowerment.
Legacy in Motion
The Urban Cabaret has become one of Madison’s most dynamic community events, not just for its entertainment, but for its mission. Each year, it brings together friends, families, and leaders to share how funds are used for the Urban League’s empowerment programs. These programs open doors to employment, entrepreneurship, and education, changing real lives in tangible ways. Supported by platinum sponsors like Ascendium, American Family Insurance, and US Bank, the evening reminded guests that progress thrives when corporate, civic, and community forces align with shared purpose.
A Decade of Vision, A Future of Hope
As the evening drew to a close, applause filled the hall—an echo of appreciation that went beyond performance. It was a standing ovation for a decade of work under Dr. Ruben Anthony’s leadership: a decade marked by courage, compassion, and consistency. In a world often divided, the Urban League of Greater Madison has remained a beacon in the community, where empowerment is not a promise—it’s a practice.
The Urban Cabaret 2025 was more than an event; it was a reflection of the heartbeat of a community that refuses to be overlooked. It celebrated art, leadership, and legacy in harmony—each note and name woven into a story that continues to unfold. As the curtains closed on this tenth anniversary, one thing was certain: the spirit of the Urban League, and the vision of those who lead it, will keep shining long after the final spotlight fades.
