Holmberg's Morning Sickness - Arizona Episode: May 22, 2025 - Steph Tolev - Tempe Improv - In Studio

Host/Author: John Holmberg with Brady Bogen, Bret Vesely, and Dick Toledo

1. Introduction to Steph Tolev's Comedy Career

In this episode, Steph Tolev joins the Holmberg's Morning Sickness (HMS) team to discuss her burgeoning career in comedy. Steph shares insights into her journey, highlighting her recent achievements and upcoming projects.

Steph Tolev: "I've gone on pretty much every podcast you can think of. I'm going to Austin to do that podcast run."
[02:15]

2. Collaborations with Porn Stars

Steph delves into her unique comedic collaborations with individuals from the adult entertainment industry. She explains how these partnerships blend humor with unexpected twists, making her content both edgy and entertaining.

Steph Tolev: "I do these like, fake jokes where I act like it's going to be dirty and then it's not."
[03:58]

One notable collaboration with Samantha Mack went viral, where Steph combines classic porn tropes with comedic subversions.

Steph Tolev: "It's a spin on, like, the classic porn tropes. And I just turned it around and make it funny instead of having a dude with this."
[04:22]

3. Journey to U.S. Citizenship

A significant portion of the conversation centers around Steph's process of obtaining U.S. citizenship. She shares her apprehensions and the humorous struggles she faces while preparing for the citizenship test.

Steph Tolev: "I'm learning about America. I'm stupid, though. I have, like, flashcards. Trying to learn. I'm screwed. I'm going to have to force my boyfriend to marry me. I'm gonna fail this for sure."
[07:19]

Steph expresses concern over her knowledge of American history and government, leading to lighthearted banter about potential study aids.

Steph Tolev: "I don't even know what they are, though. They're just things like. Yeah, that's all you need. That's it."
[07:50]

4. Relationship with Jefferson Davis McDonald

Steph introduces her boyfriend, Jefferson Davis McDonald, a classically trained pianist and comedian. Their relationship becomes a focal point as they discuss his influence on her life and career.

Steph Tolev: "He's a comedian. Performer. More musician. He sings. He plays piano."
[15:31]

Their humorous exchanges reveal a supportive and playful partnership, with Jefferson assisting Steph in her studies for citizenship.

Unknown Host: "He helps me study. He knows all the answers."
[07:35]

5. Recent and Upcoming Projects

Steph highlights her involvement in the new Netflix series "Tires", where she plays Stabby's wife. Additionally, she mentions her cameo in Bill Burr's movie "Old Dads".

Steph Tolev: "I'm in the new season of Tires on Netflix. Ridiculous. Yeah, that's fantastic. Yeah, it is very fun."
[16:52]

Steph Tolev: "I was in Bill Burr's movie. If you saw Old Dads. I didn't see it. Cameo in there."
[18:50]

She expresses excitement about reaching a broader audience through these platforms and the impact they have on her career trajectory.

6. Personal Anecdotes and Observations

Throughout the episode, Steph shares various personal stories and humorous observations, ranging from experiences at comedy clubs to quirky interactions during her tours.

a. Restroom Woes and Travel Stories

Steph discusses the challenges of maintaining hygiene standards during tours, leading to comedic reflections on public restrooms and rest stop conditions.

Steph Tolev: "I'm squatting over toilets because women are not wiping seats. I don't know what's going on up there. It's disgusting."
[17:33]

b. Handling Public Misconceptions

She humorously addresses misconceptions about her identity, particularly instances where her appearance leads to mistaken identity.

Steph Tolev: "I sound masculine. I have a mullet right now. It is confusing, but it's..."
[19:10]

7. Upcoming Performances and Final Thoughts

Steph concludes the discussion by promoting her upcoming shows at Desert Ridge Improv and Tempe Improv, encouraging listeners to support live comedy.

Steph Tolev: "Come to the show. Support live comedy. Stop just swiping away all day. That's my wisdom. Get out of your house. Stop looking at your phone and experience something."
[22:20]

Unknown Host: "That's Steph Tolev, everybody. It's 98, Arizona's most powerful rock radio station."

[22:37]

Notable Quotes

• Steph Tolev on Comedy Collaborations:
  "I do these like, fake jokes where I act like it's going to be dirty and then it's not."
  [03:58]

• Steph on Citizenship Test Anxiety:
  "I'm learning about America. I'm stupid, though. I have, like, flashcards. Trying to learn. I'm screwed."
  [07:19]

• Steph Introducing Jefferson:
  "He's a comedian. Performer. More musician. He sings. He plays piano."
  [15:31]

• Closing Wisdom from Steph:
  "Come to the show. Support live comedy. Stop just swiping away all day."
  [22:20]

Conclusion

This episode of Holmberg's Morning Sickness offers an in-depth look into Steph Tolev's multifaceted career and personal life. From her innovative comedic collaborations and upcoming projects to the humorous hurdles of becoming a U.S. citizen, Steph provides listeners with an engaging and relatable narrative. Her candid discussions, sprinkled with humor and personal anecdotes, make for an entertaining and insightful listen, even for those who might not be familiar with her work.