Matt Carr is the Manager of Special Events at Chicago’s iconic Music Box Theatre, a historic movie palace that has been bringing film lovers together on Southport Avenue since 1929. After moving to Chicago in 2011, Matt fell in love with the city’s character, neighborhood spirit, and passionate communities. His path to the Music Box took him through hospitality and luxury hotels before he found a way to turn his lifelong love of cinema into a career.

Today, Matt helps bring the Music Box’s unique programming and experiences to life, from classic and independent films to cult favorites, international cinema, and unforgettable seasonal traditions. With its starry-sky ceiling, old-school charm, and nearly century-long history, the Music Box is more than a movie theatre. It’s a Chicago institution where generations of film lovers come together to celebrate the magic of the big screen.

We also dive into the theatre’s legendary Halloween programming, including its 24-hour horror marathon and immersive screenings of classic William Castle films. Matt shares the stories behind the Music Box’s beloved Christmas traditions, the ghost said to haunt the building, and what makes Chicago such a special place to live and work. From preserving the magic of moviegoing to building community through a shared love of film, Matt explains why the Music Box continues to captivate audiences nearly 100 years after opening its doors.

In this episode, we discuss:

• How Matt found his way to Chicago and built a career around his love of cinema
• The history and enduring magic of the Music Box Theatre
• What makes the Music Box different from a traditional movie theatre
• Balancing new releases with classic, independent, international, and cult films
• The theatre’s legendary Halloween programming and 24-hour horror marathon
• Immersive William Castle screenings featuring interactive effects and audience participation
• Beloved Christmas traditions, including sing-alongs, carolers, and the theatre’s organist
• The story of “Whitey,” the ghost said to haunt the Music Box
• Why preserving the moviegoing experience matters in an increasingly digital world
• What Matt loves about Chicago’s neighborhoods, people, and passionate communities

Kenya Merritt is Commissioner of Chicago’s Department of Cultural Affairs and Special Events (DCASE), which brings some of the city’s most beloved cultural experiences to life. From the Chicago Blues Festival and Jazz Festival to Taste of Chicago, the Chicago House Music Festival, and Arts in the Dark, Kenya helps oversee the events, public art, and cultural programming that make Chicago such a vibrant place to live and visit. A University of Illinois and DePaul University graduate, Kenya has spent her career in public service, working to make Chicago a better, more accessible city for its residents and visitors.

Kenya takes us behind the scenes of the city’s cultural programming and shares what it takes to plan and produce events that bring Chicagoans together. We talk about the importance of making arts and culture accessible across every neighborhood, supporting emerging local artists, and preserving the musical traditions that have shaped Chicago’s identity. Kenya also discusses DCASE’s work with major festivals, its grant programs and resources for artists, and the events Chicagoans can look forward to throughout the fall and holiday season. From the global influence of Chicago house music to the magic of free summer festivals, Kenya shares why investing in arts and culture is essential to the city’s sense of community and belonging.

In this episode, we discuss:

• Kenya’s journey from studying pre-med at the University of Illinois to a career in public service
• Her role as Commissioner of Chicago’s Department of Cultural Affairs and Special Events
• The behind-the-scenes work that goes into producing Chicago’s major festivals and cultural events
• The impact of the Chicago Blues Festival, Jazz Festival, Taste of Chicago, and House Music Festival
• How DCASE partners with neighborhood organizations and larger festivals like Lollapalooza and Riot Fest
• The importance of making arts and cultural programming free and accessible across Chicago
• How DCASE supports local artists through grants, professional development, and its Consult DCASE program
• The significance of Chicago house music and its influence around the world
• What to expect from Arts in the Dark, World Music Festival, and Chicago’s holiday celebrations
• Why Kenya believes arts and culture are essential to Chicago’s identity, vibrancy, and sense of home

Connect with Kenya Merritt on LinkedIn here.

Listen now, and don’t forget to subscribe, rate, and comment; it helps us keep bringing you the voices behind the institutions, people, and places that make Chicago extraordinary.

Connect with the hosts of DIBS on Instagram: Nick Sarantos and Mallory Waxman

Laganja Estranja, also known as Jay Jackson, is a dancer, choreographer, drag performer, and cannabis entrepreneur who first captured national attention competing on Season 6 of RuPaul’s Drag Race in 2014. A graduate of the California Institute of the Arts with a BFA in dance and choreography, Laganja has built a career defined by fearless self-expression, creative innovation, and advocacy for LGBTQ+ visibility, human rights, and cannabis legislation. From performing on television and creating music videos to choreographing musical theater, she has continued to push boundaries and redefine what is possible for artists in the drag community.

But Laganja’s story goes far beyond the stage. In this episode of Dibs, she opens up about her career's evolution, her journey through gender transition, and the importance of separating her drag persona from her identity as Jay. We talk about how cannabis became an important part of her life after a dance injury, inspiring her to become an advocate and launch her own cannabis brand in partnership with New Era Cannabis and Sway in Chicago. Laganja also shares the business lessons she has learned as a creative entrepreneur, the challenges of navigating public scrutiny and financial uncertainty, and why trusting her intuition, embracing vulnerability, and continuing to evolve are essential to her growth. From her dream of directing a Cirque du Soleil production to her upcoming documentary about her transition, Laganja proves that the next chapter can always hold something new.

In this episode, we discuss:

• Growing up in Texas, discovering dance, and earning a BFA in dance and choreography
• Auditioning for RuPaul’s Drag Race and how Season 6 changed her career
• Building a career through strategic planning, music, merchandise, choreography, and performance
• The evolution of her drag persona and learning to separate Laganja from Jay
• Her gender transition, self-discovery, and the ongoing journey toward self-love
• How a dance injury introduced her to the medicinal benefits of cannabis
• Launching her cannabis brand with New Era Cannabis and Sway in Chicago
• Cannabis advocacy, LGBTQ+ visibility, and Chicago’s legacy of cannabis activism
• The business lessons creative people need to learn, including knowing when to build a team
• Creating her one-take music video for “Daily Basis” and the art of choreography
• Navigating mental health, public scrutiny, financial challenges, and the pressure to succeed
• Her upcoming documentary, Honoring Her: A Trail of Glitter, about her transition
• Her dreams of directing Cirque du Soleil, earning an EGOT, and continuing to evolve as an artist
• What Laganja loves about Chicago, from Boystown to the city’s pioneering cannabis community

Connect with Laganja Estranja on Instagram or her website.

Listen now, and don’t forget to subscribe, rate, and comment; it helps us keep bringing you the voices behind the institutions, people, and places that make Chicago extraordinary.

Connect with the hosts of DIBS on Instagram: Nick Sarantos and Mallory Waxman