Holmberg’s Morning Sickness – "Guadalupe Squares: MLK Day Edition" (01-16-2026)

Episode Overview

In this highly comedic MLK Day special, John Holmberg and crew present the “Guadalupe Squares,” a parody celebrity tic-tac-toe game, with each square manned by outrageous character impressions — from Barack Obama and Big Mike (Michelle Obama), to Ice T, Donald Trump, Morgan Freeman, Black Lady Brady, Tracy Morgan, Michael and Prince Jackson, and more. The cast lampoons racial identity, civil rights holiday clichés, and cultural touchstones through fast-paced, sometimes biting improv, all while engaging callers in trivia for prizes. The show walks the line between irreverence and homage, giving MLK weekend a chaotic, satirical spin.

Key Segments and Highlights

1. Setting Up the MLK Day Guadalupe Squares

[00:24 – 00:47]

• The hosts kick off the first “Guadalupe Squares” of the year, making it clear this edition will lean into MLK Day, with references to civil rights and racial humor.
• Joking suspicion around Brett’s (Bret Vesely) “excitement” about civil rights:
  “Brett loves civil rights. I don’t trust his excitement.” – John Holmberg [00:33]

2. Top Rows and Celebrity Entrants

Obama & "Big Mike" (Michelle Obama Parody)

[00:54 – 01:46]

• Barack Obama enters, soon joined by "Big Mike" (Michelle), portrayed as brashly sexual and domineering, making innuendos about pegging the ex-president in honor of her birthday.
• Memorable banter sets the tone for the episode’s bawdy, borderline absurd racial parody:
  • “Somebody getting pegged this weekend.” – Big Mike (Michelle Obama) [01:07]
  • “That’s me...” – Obama [01:11]

Ice T Tribute and "Colors" Rap Performance

[02:03 – 03:05]

• Ice T arrives, delivers a mini-rap performance of his 1988 track “Colors” — joined unexpectedly by Donald Trump, who attempts his own version.
  • "You’ve seen this movie, you gon’ live it. …Colors!” – Ice T [02:27]
  • Trump chimes in: “My colors, my honor, my colors, my all. With my colors upon me, one soldier stands tall.” [03:58]

President Trump’s Schtick

[03:08 – 04:13]

• Trump delivers a hyperbolic monologue about being beloved by "the blacks" and skewers Biden’s infamous “you ain’t black” gaffe.
  • Satirical claims of his rap skills: “A lot of people say I did it better than Ice T.” – Trump [04:01]

Morgan Freeman’s Cynical Wisdom

[04:14 – 06:52]

• Morgan Freeman laments how people only remember civil rights on MLK weekend, accusing the hosts of “crackery.”
  • “I like to celebrate civil rights every single day, unlike you crackers who just notice it when you get a three day weekend.” [04:29]
  • Roasts Cory for his whiteness: “Corey’s so white, the saltine people are suing him.” [05:37]
  • Launches into a prison rape riff about what would happen if Cory went to Shawshank.

3. Middle Rows: Comic Escalations

Black Lady Brady's Heatwave

[06:59 – 09:11]

• "Black Lady Brady" complains about Arizona’s heat in January and its effects on her “nether regions,” mixing old Southern and Black comic tropes with sexual exaggerations.
  • “I got the vapors, I’m sweating like a hoe in church!” [07:19]
  • Jokes about "Vietnam veterans in my vagina" due to the humidity [08:09]
  • Discusses giving away her toes for lemonade: “Give you four of my toes… I just need the big one.” [09:04]

Tracy Morgan and the Walmart Truck

[09:27 – 11:37]

• Tracy Morgan recounts the real-life incident of being hit by a Walmart truck, claiming it’s his “biggest payday,” and riffs about being able to “take anything off the shelf” at Walmart now.
  • “The biggest payday I ever had wasn’t some movie … but I got trucked over by a Walmart truck. And I’m a billionaire.” [09:30]
  • Teases Cory for allegedly using hot chocolate shampoo and escalates into a “Swiss dick” bit. [11:39]

Michael & Prince Jackson Confusion

[12:22 – 14:48]

• Michael Jackson appears to celebrate “African culture” with Prince, leading to a surreal riff about their racial identity (and AI duets).
  • “I want to celebrate the African culture with my son. Come on in here, Prince.” [12:34]
  • The pair attempt to sing "Ebony and Ivory."
  • Discussions about their family resemblance; Prince claims, "I was named after another African American singing hero. … Prince." [14:09]
  • Meta-humor about using the “n-word pass”: “Do you not have the pass?” – Cory / “I have it, I just won’t use it.” – Prince [26:56]

4. Prize Game – Callers, Trivia, and Rapid-fire Jokes

[15:53 – 25:54]

• Listeners Lori and Paul call in; each picks squares for a chance to win concert tickets.

• Character answers are always roundabout, full of in-character tangents:

  • Black Lady Brady extols romance on a full stomach: “I like my stomach to look like it’s covered in romance. That means we know they got the job done.” [16:51]
  • Trump improvises dark humor jokes: “I like my ladies so dark their nickname is under the bed.” [20:22]
  • Obama and Big Mike go astray, turning a question about true friendship into a double entendre about “investing 200 inches” [22:25], then break into "Give It to Me Baby."

• Technical difficulties abound; characters break the fourth wall riffing on mic issues and show production.

5. Closing Skits and Epilogue

The Jacksons Reflect on "The Black Experience"

[25:43 – 28:28]

• Prince Jackson gives a mock-serious speech about racial profiling and being “harassed by the man,” while Michael and the others joke about “privilege,” Jackson family lore, and “keeping it black.”
  • “Can’t a man like me, Prince Jackson, drive around in his Monte Carlo without getting hassled by the man?” [27:29]

Final Wrap and Next Week’s Tease

[28:29 – 28:47]

• Hosts close the show, making plans for the long weekend, poking fun at Cory’s sports fandom and their own irreverence.

Memorable Quotes

• Obama (as himself):
  “That’s me. My wife’s probably gonna peg me all weekend long in honor of her birthday.” [01:11]

• Morgan Freeman:
  “I like to celebrate civil rights every single day. Unlike you crackers who just notice it when you get a three-day weekend.” [04:29]

• Black Lady Brady:
  “Scummy Dick Douglas found two Vietnam veterans living inside my vagina, ‘cause it’s so humid down there.” [08:16]

• Trump:
  “I like my ladies so dark their nickname is under the bed. …Acme dark is what I’m saying.” [20:22]

• Tracy Morgan:
  “I can walk right into a Walmart, just take what I want off the shelf and leave. They say: ‘That’s Tracy Morgan, he’s allowed to have anything he wants.’” [09:30]

• Prince Jackson:
  “I was named after another African American singing hero. …Prince.” [14:09]

Standout Comic Bits & Moments

• Trump’s tone-deaf “Colors” rap and bizarre racial one-liners [03:08 – 04:13; 20:20]
• Morgan Freeman eviscerating Corey for his “Ultra-whiteness” and “Pixar marathons” [05:07]
• Multiple characters breaking into song — “Ebony and Ivory,” "Give It to Me Baby" [13:13; 22:42]
• Black Lady Brady’s extended rant about the desert heat and body parts [06:59 – 09:11]
• Tracy Morgan’s relentless Walmart riff and fixations on mayonnaise, Oreos, and Cory’s “hot chocolate dick” [09:27 – 11:37]
• Meta-commentary about technical difficulties, characters roasting the host and themselves

Major Timestamps

• 00:24 – 00:47: Start of Guadalupe Squares, introducing the MLK theme
• 00:54 – 01:46: Obama and Big Mike routine
• 02:03 – 03:05: Ice T “Colors” performance, joined by Trump
• 04:14 – 06:52: Morgan Freeman’s civil rights skepticism and roast
• 06:59 – 09:11: Black Lady Brady’s Arizona heat rant
• 09:27 – 11:37: Tracy Morgan on Walmart/the payout bit
• 12:22 – 14:48: Michael & Prince Jackson, confusion about race/paternity
• 15:53 – 25:54: Prize game with callers, in-character answers and running jokes
• 25:43 – 28:28: Prince Jackson mock-reflection on “The Black Experience”
• 28:29 – 28:47: Episode wrap-up and banter

Tone & Style

The episode maintains a rollicking, no-holds-barred, rapid-fire energy throughout, with irreverent parody, meta-commentary, and topical in-jokes. Characters lean into racial and political stereotypes for comic effect, often subverting expectations with absurdity or pointed social parody, all while keeping the game show moving for callers.

This summary pulls together all major segments, standout moments, and best jokes, making it easy for new listeners to jump in on Holmberg’s Morning Sickness’ signature blend of edgy, topical satire and character-driven improv.