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.

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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

Ben Zobrist is a three-time MLB All-Star, two-time World Series champion, and the 2016 World Series MVP whose clutch double in Game 7 helped the Chicago Cubs end their 108-year championship drought. An Illinois native, Ben spent 14 seasons in Major League Baseball, playing for teams including the Tampa Bay Rays, Kansas City Royals, and Chicago Cubs. He became part of baseball history during one of Chicago's most unforgettable moments, helping bring a championship to a city and generations of fans who had waited more than a century.

But Ben’s story goes far beyond baseball. In his new book, Prepare for the Pressure: Nine Strategies to Be Courageous, Consistent and Resilient When It Matters Most, he opens up about the emotional challenges and depression he experienced after the Cubs’ historic victory, and what it meant to find himself struggling after reaching the pinnacle of his career. We talk about the pressure of professional sports, the importance of therapy and mental health, and learning to find an identity beyond the uniform. Ben also shares how his experiences inspired Champion Forward, an organization that helps young athletes and families develop mental and emotional skills.

In this episode, we discuss:

• Growing up in Illinois and building a 14-year career in Major League Baseball
• Winning the World Series with the Kansas City Royals and Chicago Cubs
• His unforgettable double in Game 7 of the 2016 World Series
• What it was like to be part of the Cubs’ historic championship run
• The depression and emotional challenges he faced after winning it all
• The importance of therapy, mental health, and asking for help
• Learning to separate personal identity from professional success
• His new book, Prepare for the Pressure, and strategies for building resilience
• How Champion Forward supports young athletes and their families
• Finding purpose and fulfillment beyond the baseball field

Connect with Ben Zobrist on Instagram and get a copy of his book, Prepare for the Pressure, 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

Dwight White II, is a painter, muralist, and creative storyteller whose work captures the people, places, and moments that make Chicago special. Originally from Houston, Dwight came to Chicago as a highly recruited linebacker for the Northwestern Wildcats, with dreams of building a career in football.

But after a medical issue forced him to walk away from the sport, Dwight found himself facing an unexpected question: What happens when the life you planned for yourself suddenly changes?

For Dwight, the answer was art. What began as therapy during a difficult period eventually became a career. Today, his work includes large-scale murals, original paintings, and collaborations with professional sports teams, universities, nonprofits, and major brands.

We also dive into Dwight’s deep connection to Chicago, his work with the Innocence Project and After School Matters, his Derrick Rose mural, and the Northwestern Black House mural. We talk about how his athletic background shaped his creative career, why he believes artists should trust their instincts, and what still inspires him about the city he now calls home.

In this episode, we discuss:

• Growing up in Houston and playing football at Northwestern
• The injury that forced him to walk away from football
• How art became a form of therapy and eventually a career
• The intersection of sports, art, branding, and fandom
• His work with the Innocence Project, After School Matters, and Derrick Rose
• Returning to Northwestern to create a mural at the Black House
• Why artists should trust their instincts and embrace being different
• How his athletic background shaped his approach to art
• Why Chicago became home and continues to inspire his work

Connect with Dwight White via his website or his Instagram.

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

We’ve got dibs on Dr. Mary Ellen Caron, CEO of After School Matters, one of the nation’s largest and most respected providers of after-school and summer programming for teenagers.

For more than a decade, Mary Ellen has led After School Matters, helping thousands of Chicago teens develop skills, explore careers, find their people, and discover opportunities they may not have otherwise had. Today, the organization serves more than 11,000 teens through programs in the arts, STEM, sports, leadership, communications, and skilled trades.

But Mary Ellen’s commitment to young people started long before After School Matters. She began her career as a teacher on Chicago’s West Side before becoming the founding principal of the Francis Xavier Ward School and later serving as commissioner of the Chicago Department of Children and Youth Services and the Department of Family and Support Services.

In this episode, we talk about why After School Matters was created, the importance of giving teenagers meaningful opportunities outside of school, and why the organization pays teens to participate in its programs. We also talk about the real-world skills young people develop, from communication and collaboration to resume writing and interviewing.

We dive into some of After School Matters’ partnerships across Chicago, including its work with the Chicago Bulls, local museums, ComEd, and the Obama Presidential Center, and how these experiences give teens a chance to see themselves in careers and spaces they may have never imagined.

And perhaps most importantly, Mary Ellen shares why finding your people can be just as important as finding your career path. Whether it’s theater, jazz, culinary arts, dance, or skilled trades, After School Matters gives Chicago teens a place to explore what they love, build confidence, and figure out what comes next.

We also talk about Mary Ellen’s vision for her legacy, her love of Chicago, and why she believes the city is better because After School Matters exists.

After School Matters Website

Learn more about the After School Matters Gala 2026 on Thursday, September 24, 2026 at the Obama Presidential Center Home Court

Listen now and don’t forget to subscribe, rate, and comment; it helps us continue to bring 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

We sit down with Adam Pearce, WWE's General Manager of Monday Night Raw and a five-time NWA World Heavyweight Champion. Before becoming one of the most recognizable faces on WWE television, Adam spent decades grinding on the independent wrestling circuit, refusing to give up on the career he believed was possible.

Growing up in Waukegan, Adam dreamed of playing college football until a devastating injury changed the course of his life. That unexpected setback led him to professional wrestling, where perseverance, resilience, and an unwavering belief in himself ultimately brought him to the biggest stage in sports entertainment.

We also dive into his deep Chicago roots—from growing up in Lake County and cheering on the Cubs (while somehow remaining a Packers fan), to why Chicago wrestling fans are unlike any other, his favorite neighborhood, pizza spot, and what it means every time WWE returns to the city he still proudly calls home.

Whether you're a lifelong wrestling fan or have never watched a match, this conversation is about far more than wrestling. It's about chasing your dreams, embracing unexpected paths, and never giving up on what's possible.

In this episode, we discuss:

• How a football injury unexpectedly led Adam to professional wrestling
• Spending nearly two decades on the independent wrestling circuit before joining WWE
• The importance of resilience, patience, and trusting the process
• Behind-the-scenes stories from WWE and working with today's biggest superstars
• Why Chicago remains one of wrestling's greatest cities
• His favorite Chicago neighborhood, pizza spot, and sports memories
• Balancing life on the road with family and fatherhood

Listen now and don’t forget to subscribe, rate, and comment; it helps us continue to bring 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

From Office Space and Talladega Nights to The West Wing, NCIS, and more than 200 film and television credits, Gary Cole has built one of the most recognizable careers in Hollywood. But before the iconic roles, there was Chicago.

Gary joins us while back in Chicago, performing in Steppenwolf Theatre Company's production of Catch as Catch Can, marking his long-awaited return to the Steppenwolf stage. As one of the theater's original ensemble members, Gary reflects on Steppenwolf's beginnings in a church basement in Highland Park, the friendships that shaped his career, and why Chicago has always remained home.

We also dive into his legendary career on screen, the differences between theater, film, and voice acting, the surprising legacy of Office Space, and why mentorship remains one of the most meaningful parts of his career.

Whether you've known him as Bill Lumbergh, Alden Parker, Mike Brady, or one of his countless other unforgettable characters, this conversation offers a rare look behind the scenes of an actor whose work has become part of pop culture history.

• Gary's childhood growing up in the Chicago suburbs
• The early days of Steppenwolf Theatre and its remarkable evolution
• Returning to the stage for Catch as Catch Can
• Why is this production one of the most challenging of his career
• The differences between theater, television, film, and voice acting
• Behind-the-scenes stories from Office Space and its enduring legacy
• Building a career that spans more than four decades
• The importance of mentorship and supporting the next generation of actors
• What Chicago continues to mean to him after all these years

Tickets and show information for Catch as Catch Can can be found here

Listen now and don’t forget to subscribe, rate, and comment; it helps us continue to bring 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