The king of the roast chair takes a thoughtful turn as legendary comedian Jeff Ross joins Second Thought with Suzy Weiss, now streaming on YouTube.
Known worldwide as the “Roastmaster General,” Ross sits down with Weiss for a wide-ranging conversation that explores the deeper truths behind a career built on sharp punchlines and fearless commentary.
For decades, Ross has been one of comedy’s most recognizable voices, delivering unforgettable roasts of cultural icons ranging from Joan Rivers and Justin Bieber to Charlie Sheen. In this candid discussion, he argues that roast comedy remains one of the last public spaces where truly unfiltered commentary can still thrive, offering audiences an outlet for honesty, humor, and cultural reflection.
The conversation centers around Ross’s acclaimed Netflix special, Take a Banana for the Ride, a deeply personal project that blends his signature humor with poignant reflections on loss and resilience. Ross opens up about losing both of his parents as a teenager, the lasting impact of grief on his life, and how comedy became a powerful tool for healing, self-preservation, and developing the thick skin that would ultimately define his career.
Beyond the special, Ross shares behind-the-scenes stories from some of comedy’s biggest events, including how The Roast of Tom Brady unexpectedly helped ease long-standing tensions between Brady, his former team, and Bill Belichick. He also reveals how he convinced Brady to return to the roast stage for The Roast of Kevin Hart, offering a rare glimpse into the relationships and negotiations that happen away from the spotlight.
Ross and Weiss also tackle several cultural flashpoints, including the reemergence of the word “retarded” in public discourse, the evolving boundaries of comedy, and Ross’s relationship with President Donald Trump. The interview balances provocative social commentary with personal storytelling, including Ross’s heartfelt account of adopting a geriatric dog during the pandemic and the unexpected lessons that experience taught him.
Equal parts hilarious, insightful, and deeply human, Jeff Ross’s appearance on Second Thought with Suzy Weiss showcases a side of the comedy icon that audiences rarely get to see. It’s a revealing conversation about loss, resilience, free expression, and why laughter remains one of life’s most powerful coping mechanisms.
Watch Jeff Ross’s full appearance on Second Thought with Suzy Weiss now streaming on YouTube
