In the episode titled “Heartbreak and the Refuge of the Downtrodden,” we find Connor McAllister, portrayed by Dougie Baldwin, in a deep rut. His lifeline comes in the form of music, prompting him to focus on his musical aspirations. Connor sends one of his tracks to the legendary Doctor Demento, mentor to Weird Al Yankovic. The song, “Do The Axolotl,” eventually catches the attention of a delighted Demento in Los Angeles. Although the retired radio icon, whose real name is Barret Eugene “Barry” Hansen, is only shown from the back, his approving reaction is unmistakable, and he is credited as playing himself.

This marks a significant moment as Doctor Demento becomes the first celebrity to make an onscreen cameo on “Georgie and Mandy’s First Marriage.” The inclusion of a celebrity in the otherwise ordinary world of the show fits its narrative style, known for weaving famous personalities into its storylines. For instance, “The Big Bang Theory” featured guest appearances by Stephen Hawking and Carrie Fisher among other notable figures. Similarly, “Young Sheldon” saw brief appearances by stars like David Hasselhoff and Elon Musk. However, one might question the necessity of Dr. Demento’s appearance, given that Connor already has a well-connected ally.

In Season 1’s episode “Secrets, Lies and a Chunk of Change,” it’s revealed that Connor has a friendship with Jay Leno. Initially, the McAllister family doesn’t pay much heed to this claim until they hear a voicemail from Leno himself, inviting Connor to join “The Tonight Show” band whenever he visits. Although Leno lent his voice to the episode, unlike Doctor Demento, he didn’t appear on screen.

As mentioned in Season 1’s “Secrets, Lies and a Chunk of Change,” Connor is friendly with Jay Leno. The McAllisters are initially unimpressed by this bit of news  — until Leno leaves a message on the family’s answering machine. In the voicemail, the comic tells Connor that he’s welcome to come be a part of the history of “The Tonight Show” and sit in with his house band any time he’s in town. Jay Leno provided his own voice for the episode, making him the show’s first celebrity guest — though, unlike Doctor Demento, he never appears on-camera.

But if Connor already has an influential associate, why does he need to have his work played on the radio by a stranger? Dougie Baldwin has a theory about that. “Jay’s just his buddy. He’s just his friend. He’s not trying to go work for him — he’s just like, ‘That’s my friend,’” the actor told TVLine. But he wouldn’t say no to Connor making his West Coast debut. “Listen, that’s in the hands of the producers. I would love to go hang out with Jay Leno and pretend to play in his band. That would be such a funny turn.” While Connor’s future remains unwritten for now, it’s clear he’s got big plans — hopes and dreams that might make him a huge music star and take him out of Texas for good, or leave him high and dry in the end.