Podcast Summary: The Dan Le Batard Show with Stugotz – South Beach Sessions featuring Andrew Santino and Bobby Lee

Release Date: December 12, 2024

Introduction

In the December 12, 2024 episode of "South Beach Sessions" from The Dan Le Batard Show with Stugotz, host Andrew Santino welcomes comedian and actor Bobby Lee. Filmed at the vibrant Elser Hotel in Downtown Miami, the episode delves deep into Bobby Lee’s comedic journey, personal struggles, and his dynamic friendship with fellow comedian Andrew Santino.

Bobby Lee’s Career Evolution

Andrew initiates the conversation by exploring Bobby Lee's comedic roots and his evolution over the years. Bobby shares insights into his podcast ventures:

Bobby Lee [01:24]: “We started Bad Friend. I started Whiskey Ginger about seven and a half years ago. In 2020, we launched Bad Friends with Bobby Lee, which really catapulted us in the internet space.”

Bobby reflects on the sudden fame brought about by his podcast, highlighting both its perks and challenges:

Bobby Lee [02:05]: “I can't walk down the street without someone crossing their eyes and yelling, 'I'm Bobby, Mom.' That happens daily. It's a blessing and a curse.”

Friendship and Collaborations

A significant portion of the episode focuses on Bobby Lee’s friendship with Andrew Santino. Bobby describes their unique chemistry and mutual respect:

Bobby Lee [05:23]: “My friendship with Bobby is a peculiar one. We are polar opposites, but we love each other so much despite having nothing in common on paper.”

They discuss how their collaborative efforts have resonated with audiences, comparing their duo to legendary comedic pairs like Martin and Lewis:

Bobby Lee [03:58]: “It's not only the best thing I've ever done creatively and comedically, but it's also so culturally relevant.”

Overcoming Addiction

Bobby Lee candidly addresses his struggles with addiction and the impact it had on his life and career. He recounts the difficult decision to encourage a friend to seek rehab, emphasizing the depth of their bond:

Bobby Lee [10:51]: “The first time we put him in rehab, he had an epiphany about what he really wanted in life... It was a loving act.”

Drawing from his personal background, Bobby reflects on how his father's battles with addiction shaped his perspective:

Bobby Lee [11:01]: “I'm a child of addiction. My dad was an addict who was in and out of prison when I was a kid. I make light of it because it's the only way I can deal with it.”

Comedy Chemistry and Personal Relationships

Andrew probes into what makes Bobby Lee's comedic relationships so special. Bobby praises his interactions with other comedians while emphasizing his unique bond with Andrew:

Bobby Lee [15:31]: “Rick Glassman and I have been friends for a long time. But with Bobby, it is something different. There's a love that's so real that makes the comedy so fun.”

Their discussion touches upon the importance of genuine connections in comedy, transcending mere professional relationships.

Life Before Comedy

Bobby Lee shares his pre-comedic days, detailing his move to Los Angeles and the struggles he faced:

Bobby Lee [22:22]: “I moved on the 4th of July in a U-Haul while the fireworks were going off. I had no money and lived in a partitioned space with strangers.”

He humorously recounts his early jobs and the challenges of balancing day jobs with his passion for comedy:

Bobby Lee [29:31]: “I worked as a PA, doing endless errands for $400 a week before taxes. I hated it, but fun was all I was good at.”

Achievements and High Points

Reflecting on his career milestones, Bobby highlights moments that brought him immense joy and fulfillment:

Bobby Lee [34:17]: “Landing my first gig for MSN was one of the happiest moments of my life. It allowed me to quit my day job and pursue comedy full time.”

He also shares his admiration for working with comedy legends like Larry David and Julia Louis-Dreyfus:

Bobby Lee [61:02]: “Making Larry laugh was one of the best moments of my career. Julia Louis-Dreyfus' laughter was unforgettable.”

Balancing Multiple Projects

Bobby discusses the complexities of juggling multiple projects, including podcasts, stand-up tours, and new television ventures:

Bobby Lee [41:06]: “I'm balancing two shows, a stand-up career, a new hour, and projects in the golf space. It's a lot, but it's what I want to do next.”

He candidly acknowledges the pressures that come with expanding his career:

Bobby Lee [41:47]: “I'm addicted to golf. It's bad. I literally went to San Diego yesterday and drove back last night.”

Personal Life and Marriage

The conversation shifts to Bobby Lee’s personal life, where he discusses his marriage and the challenges of maintaining privacy:

Bobby Lee [56:53]: “I am married to a woman. We've been married since 2016. She chose to keep her life private, which I respect.”

He emphasizes the importance of his wife's comfort and their mutual understanding of his public life:

Bobby Lee [52:47]: “She doesn't want to be involved in the business or the public eye. It’s important to protect her privacy.”

Future Projects and Plans

Looking ahead, Bobby shares his aspirations and upcoming projects, including a new special for Hulu and ventures into the sports comedy space:

Bobby Lee [43:03]: “We're starting a golf project because I'm a die-hard golfer. There's not a lot of comedy in the golf space, so we’re aiming to change that.”

He expresses excitement about expanding his comedic horizons while staying true to his passions:

Bobby Lee [63:40]: “The Freeze Peach Tour is going on right now. I’ve got 20 cities left before heading to Australia, New Zealand, and Singapore.”

Conclusion

The episode wraps up with Bobby Lee promoting his ongoing projects and tours, while also humorously addressing his beef with fellow comedian Adam Ray:

Bobby Lee [62:19]: “Every room turned into an escape room. I was extremely vulnerable.”

Andrew Santino concludes by highlighting Bobby Lee’s unmatched live performances:

Andrew Santino [65:33]: “Freeze Peach Tour. If you want to see him live in his natural environment, that's right where I'm the best.”

Notable Quotes with Timestamps

• Bobby Lee [02:41]: "It's the most fun I've ever had in my entire career."
• Bobby Lee [11:01]: "I'm a child of addiction. My dad is an addict who's been sober for a long time now."
• Bobby Lee [15:31]: "Rick Glassman and I have been friends for a long, long time."
• Bobby Lee [34:17]: "Landing my first gig for MSN was one of the happiest moments of my life."
• Bobby Lee [43:03]: "I'm addicted to golf. It's bad."
• Bobby Lee [56:53]: "We've been married since 2016."

Key Takeaways

• Career Growth: Bobby Lee’s journey from struggling comedian to a recognized podcast host and actor showcases his resilience and dedication to his craft.

• Importance of Friendship: His deep bond with Andrew Santino has been pivotal in his career, providing both personal and professional support.

• Overcoming Adversity: Bobby’s candid discussion about his and his friend's battles with addiction highlights the challenges faced behind the scenes of a successful career.

• Balancing Act: Managing multiple projects while maintaining personal relationships and mental health remains a central theme in Bobby Lee’s narrative.

• Future Aspirations: Bobby is keen on exploring new territories in comedy, particularly in the sports domain, indicating his desire to innovate and expand his comedic repertoire.

This episode of "South Beach Sessions" offers an intimate glimpse into Bobby Lee’s life, blending humor with heartfelt revelations. Listeners gain a deeper understanding of the man behind the laughter, his struggles, triumphs, and the relentless pursuit of his passion for comedy.