From Ross the Intern to RuPaul’s Drag Race | Ross Mathews on 25 Years in Hollywood

On this episode of Duke’s Download, I sit down with the one and only Ross Mathews — and we cover 25 years of hustle, reinvention, visibility, and straight-up staying power in Hollywood.

From being “Ross the Intern” on The Tonight Show with Jay Leno to Chelsea Lately, The Drew Barrymore Show, RuPaul’s Drag Race, and hosting the 90 Day Fiancé Tell Alls, Ross has built a career that most people couldn’t script if they tried.

We talk about:

• The moment he saw “Hello Ross” on a building (full circle moment)
• How he’s stayed relevant for 25 years in entertainment
• Losing nearly 80 pounds and transforming his health
• The “90/10” mindset that changed his relationship with food
• Grief after losing his mom and how it reshaped his life
• LGBTQ+ visibility then vs now
• The cultural impact of RuPaul’s Drag Race
• Why backlash can’t undo progress
• Marriage, love, and having a safe place to land

Ross also shares what it was like writing the children’s book Tío and Tío with his husband Wellington (Welly), inspired by their Mexico wedding — and yes, there’s a sequel coming.

We even get into his next chapter: a cookbook (Rossipes), game show dreams, and what reinvention really looks like after decades in the spotlight.

This episode is about longevity, growth, queer visibility, health, identity, and building a life that feels aligned — not just impressive.

If you’ve ever wondered how someone stays authentic in Hollywood for 25 years… this one’s for you.

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