Nick revisits one of Jay Pharoah’s funniest original creations from his Saturday Night Live years: Principal Daniel Frye of Booker T. Washington High School. While Pharoah is best known for his uncanny impressions of Barack Obama, Chris Rock, Denzel Washington, and more, Principal Frye proved he could also deliver side-splitting original characters.

The sketches feature the Principal’s absurd morning announcements, with help from guest hosts like Paul Rudd, Christina Applegate, Kerry Washington, and Anna Kendrick. Nick shares behind-the-scenes details about how the character came to life, and even tells the story of how Justin Bieber nearly derailed one of Frye’s funniest appearances.

It’s a tribute to one of SNL’s most underrated cast members and a reminder of just how funny Jay Pharoah’s tenure really was. [EP 141]

Rachel, a loyal listener and subscriber, asked for it, and Nick delivers: the unforgettable night Betty White hosted Saturday Night Live. On May 8, 2010, following a grassroots Facebook campaign, the comedy legend took the stage for a Mother’s Day episode that pulled in the season’s highest ratings and won her an Emmy.

The show featured a reunion of powerhouse female cast members — Tina Fey, Amy Poehler, Maya Rudolph, Ana Gasteyer, Rachel Dratch, and Molly Shannon — who brought back classic characters while teaming up with White in sketches that were hilariously naughty and delightfully vulgar. At 88 years old, Betty White proved she was game for anything, and the results were comedy gold.

Along with clips from that night, Nick shares behind-the-scenes stories, backstage moments, and why this episode remains one of the most beloved in SNL history. [EP 140]

Nick dives into one of Saturday Night Live’s strangest recurring sketches, Jason Sudeikis’ “Maine Justice.” Set in a Bangor courtroom where everyone sounds like they’re straight out of Louisiana, the sketch features Judge Marshall T. Boudreaux (Sudeikis), with appearances alongside Jamie Foxx and Justin Timberlake. Nick plays both performances in full, explores how the idea came to life, and shares an interview with Sudeikis and Seth Meyers breaking down the world of “Maine Justice.”

The episode also highlights a connected oddball gem, “Potato Chip,” a sketch that features the same character and just as much off-the-wall humor. Fun fact: “Potato Chip” was the subject of the very first episode of THAT SHOW…, making this a full-circle return to the weird brilliance of Sudeikis’ comedy. [EP 139]

Nick shines a spotlight on the rare group of underage performers who were tapped to host Saturday Night Live. Christina Ricci, Jennifer Love Hewitt, Sara Gilbert, Claire Danes, Miley Cyrus, the Olsen Twins, Fred Savage, and Macaulay Culkin all stepped onto the stage between the ages of 11 and 19, and their youthful energy shaped the sketches in some surprising ways.

With behind-the-scenes stories and context, Nick breaks down how each of them handled the pressure. Some rose to the occasion with strong monologues and memorable sketches, while others—yes, the Olsen Twins—struggled to make an impact. From a college dorm mix-up to a Memorial Day barbeque gone off the rails, the episode revisits some of the most unusual material these young hosts ever had to deliver.

A fun trivia note caps things off: all but one of these underage hosts only took on the job once, making their appearances even more of a fascinating footnote in SNL history. [Ep 138]

By listener request, Nick dives deep into the bizarre and brilliant world of Colleen Rafferty, one of Kate McKinnon’s most unforgettable Saturday Night Live characters. Whether she’s being abducted by aliens, haunted by ghosts, or hurled through time, Colleen’s wildly unglamorous take on supernatural events is always hilarious—and McKinnon’s commitment to the role has left both the audience and her fellow cast members in stitches. Nick revisits standout sketches, including the infamous Ryan Gosling episodes (where he breaks every time), plus appearances with Casey Affleck, Natasha Lyonne, and a star-studded take from the SNL 50th Anniversary Special featuring Pedro Pascal, Jon Hamm, Woody Harrelson, and Meryl Streep as Colleen’s mom. A filthy, funny, fan-favorite tribute to a true SNL legend. [Ep 137]

Before the monologue, before the music, it all starts with the Cold Open. Nick looks back at the iconic opening sketch format that has kicked off nearly every Saturday Night Live since its debut. From absurd beginnings like “feeding your fingertips to the wolverines,” to sharp political parodies featuring Tina Fey as Sarah Palin, Will Ferrell’s George W. Bush, and Amy Poehler’s Hillary Clinton, the Cold Open has always set the tone. Nick revisits six standout segments, sharing behind-the-scenes stories and context, all leading up to that legendary line: “Live from New York, it’s Saturday Night!” [Ep 136]

Nick uncorks a deep dive into one of Saturday Night Live’s most chaotic and beloved characters: Drunk Uncle. Created by Colin Jost and Bobby Moynihan, and hilariously portrayed by Moynihan, Drunk Uncle stumbled his way through a series of gloriously incoherent rants on Weekend Update. Whether he was griping about millennials, politics, or why everything used to be better, his politically incorrect tirades somehow remained laugh-out-loud funny.

Nick shares stories behind the creation of the character, including Moynihan’s own insights into how Drunk Uncle came to life. He also pulls back the curtain on some behind-the-scenes moments and plays back some of the most outrageous segments, complete with colorful commentary.

Expect classic cameos too, like Aaron Paul as the twitchy “Meth Nephew” and John Goodman as the even sloppier “Drunker Uncle.” It’s a booze-soaked tribute to one of SNL’s weirdest and most memorable creations, and a celebration of Bobby Moynihan’s comedic genius. [Ep 135]

Nick takes a hilarious stroll through one of SNL’s most unforgettable Weekend Update staples: The Girl You Wish You Hadn’t Started a Conversation With at a Party. Brought to life by Cecily Strong, the character is a perfect storm of chaotic energy, social cluelessness, and half-formed outrage, all filtered through a haze of phone-checking and wildly misguided opinions.

The episode dives into how this brilliantly jumbled creation came to be, with behind-the-scenes insights from Strong’s record-breaking 11-season run. Nick shares some lesser-known facts about her surprise sketch with Reese Witherspoon, who loved the character enough to crash the party as her equally unfiltered best friend. There’s also a breakdown of The Girl’s most memorable rants on topics like elections, the holidays, and the coronavirus.

You’ll also hear about how Norm Crosby’s old-school malapropisms and the lovable wreck that is Drunk Uncle played into the DNA of the character, even becoming the father of her child. It’s a fun and nostalgic look at one of the greats to ever take the Update desk. [Ep 134]

Nick returns to the oddball corner of Saturday Night Live with another dive into the infamous 12:50 sketches. These are the sketches that are too strange, too awkward, or too experimental to air any earlier, so they’re tucked away at the end of the show when the audience thins out and the rules seem to loosen.

This collection includes appearances by Anna Faris, Alec Baldwin, Catherine O’Hara, and even Oprah Winfrey. Sketches range from a woman wearing a wedding dress to a funeral, to a server working a diner shift while missing a shoe, to a calendar full of deformed male models that draws an unusual kind of admiration. There’s also a detour into the legend of Bill Brasky and a truly wild musical moment featuring Billy Joel’s “Goodnight Saigon” with surprise cameos from Tom Hanks, Anne Hathaway, Paul Rudd, and others.

As always, Nick unpacks the behind-the-scenes details and explains how these wonderfully strange sketches found their way into one of the most unpredictable time slots in television. [Ep 133]

Nick dives into the legacy of one of SNL’s most gloriously unhinged characters—Herb Welch, the crusty, confused, and wildly inappropriate newsman brought to life by Bill Hader. Inspired by a listener’s email, this episode revisits every appearance Herb ever made, complete with microphone assaults, accidental racism, and the kind of chaotic energy only Hader could channel live on air.

Alongside the audio clips, Nick offers behind-the-scenes trivia, explores the origin of the character, and reflects on Hader’s brilliant tenure at Studio 8H. From smacking Jesse Eisenberg in the face to completely derailing scenes with Anne Hathaway and Emma Stone, Herb Welch was an old-school reporter who had no business still being on air—and that’s exactly what made him unforgettable.

It’s a nostalgic, hilarious tribute to a character that represents everything unpredictable and perfect about live sketch comedy. [EP 132]