The BOB & TOM Show Free Podcast

B&T Extra: Comedian Derrick Stroup

Date: September 4, 2025
Guest: Derrick Stroup

Episode Overview

This B&T Extra episode sees the BOB & TOM crew welcome stand-up comedian Derrick Stroup for a fast-paced, comedic conversation. The main theme centers on airport and airline mishaps, with plenty of jokes, playful ribbing, and a deep dive into the quirks of the Denver airport and the world of airline seating. The hosts and Derrick riff on travel woes, the peculiarities of modern conveniences like digital tickets, and Southwest Airlines' unique boarding system—all with their hallmark wit.

Key Discussion Points & Insights

1. Denver Nuggets Hat and Team Misidentification

[03:05–04:35]

• The crew quizzes Derrick on the sports team hat Tom is wearing, which sparks banter about team logos and states.

• Notable Moment: Derrick humorously guesses "The Confederacy" after failing to identify the Denver Nuggets logo at a distance, leading to playful teasing around historical (and hysterical) misunderstandings.

  • Quote:
    "I believe that's 1862. That's the Confederacy." — Derek Stroup (03:30)

• Baseball bats, pickaxes, and skiing all get thrown into the mix before Bob reveals it’s the Denver Nuggets, further highlighting how the logo can be confusing.

2. Denver Airport Woes and Travel Stories

[05:03–10:36]

• Tom and Derrick bond over shared experiences with Denver and its infamous airport, including high Uber costs, constant construction, and inconvenient distance from the actual city.

  • Quote:
    "There's no way I'm taking a $75 Uber to take an $85 United flight." — Tom (05:23)

• Tom affectionately refers to Denver as the "connection city," noting its convenience for direct flights, but bemoans the never-ending construction and logistical headaches surrounding travel there.

• Derrick launches into a story about almost missing his flight due to confusing construction layout, unclear gate changes, and a lack of announcements or text updates from the airline.

  • Quote:
    "If you've ever been to the Denver airport, when you look at TSA, it's like looking at a photograph of Ellis Island, but there are more people there." — Derek Stroup (09:45)

3. Airline Boarding Mishaps, Digital Tickets, and Southwest's System

[10:36–14:23]

• The group debates airline boarding procedures, with Derrick expressing a preference for paper ("hard") tickets because technology "scares" him, getting laughed at for being "old-fashioned."

  • Quote:
    "That phone thing really scares me." — Derek Stroup (12:07)

• The conversation shifts to Southwest's unique open seating, inspiring Tom to vent about the stress and confusion of boarding order, and his dislike of passengers who downplay the importance of assigned slots.

  • Quote:
    "You don't feel that way when you're in middle seat in row 42!" — Tom (14:00)

• Discussion of people playing Candy Crush instead of showing their boarding position, with Tom recalling a time he defended his wife from being pushed back in line, highlighting social awkwardness and the need for airline etiquette.

  • Quote:
    "I took her ticket, and I went through the line... 'A30? Head on back, big dog!'" — Tom (14:50)

• The crew jokes about comedians faking an injury to get into pre-boarding (15:23), ribbing each other about travel hacks and “heroes” of airline seating charts.

4. Conspiracy Theories and Legends about Denver International Airport

[09:57–10:36]

• Tom brings up the popular conspiracy theories about Denver Airport—including rumors about underground buildings, signs referencing aliens, and the infamous blue Mustang sculpture known as "Blucifer."
  • Quote:
    "There's, like, a lot of conspiracy theories with that airport... They lean into it." — Tom (09:57)
  • The hosts laugh about how DIA’s marketing cheekily references these rumors in construction delay signage.

Notable Quotes & Memorable Moments

• On confusing airport info:
  "I was literally sitting there for two hours, and I finally look up. I go, what is this thing in a board? So I walk up to the guy and I go, when is this flight boarding? Because, oh, we changed the gate. Said, well, maybe an announcement would have been nice." — Derek Stroup (08:13)

• On digital tickets:
  "That phone thing really scares me. Yeah. I hate to break it to you." — Tom (12:07)

• On Southwest’s boarding culture:
  "We're all trying to—he would not just share your position, because I'm somebody, you know... It doesn't matter, we're all going to the same place. And I go, you're a psychopath, man. You don't feel that way when you're in middle seat in row 42!" — Tom (13:36)

Timestamps for Key Segments

• 03:05 — Denver Nuggets Hat Misidentification/Banter
• 05:03 — Denver Travel, Airport Complaints
• 08:13 — Gate Change and Comedy of Travel Errors
• 09:57 — Denver Airport Conspiracy Theories
• 10:36 — Hard vs. Digital Tickets and Tech Anxiety
• 12:07 — Old-Fashioned Travel Habits
• 13:30 — The Madness of Southwest Open Seating
• 14:50 — Tom Defends His Wife’s Boarding Place
• 15:23 — Pre-Boarding Faker Anecdote

Episode Tone and Style

The show maintains its quick-witted, light-hearted, and improvisational style throughout. Most of the humor stems from the crew’s personal gripes and light self-deprecation, punctuated by Derrick’s earnest, slightly bewildered traveler persona. The banter is affectionate but sharp, making the everyday frustrations of travel the heart of the comedy.

Summary for the Uninitiated

If you’ve ever been confused by an airport, annoyed by airline boarding chaos, or bewildered by “that phone thing,” this episode is for you. Derrick Stroup’s relatable tales of travel folly, paired with the BOB & TOM crew’s relentless joking and clever asides, turn ordinary pains into comedic gold. The episode delivers quick-fire jokes, relatable anecdotes, and a tongue-in-cheek look at the madness modern air travel can bring.