Surely You Can't Be Serious Podcast

The madness continues. In Part 2 of their deep dive into the now-infamous Star Wars Holiday Special, Jason and Dee of Surely You Can’t Be Serious are once again joined by the guys from the 30something Movie Podcast to finish what they started. Having already crossed the point of no return, the crew pushes through the remaining skits, songs, and baffling story choices that somehow made it onto television. More celebrity appearances surface, the variety-show chaos escalates, and the line between endurance test and pop-culture archaeology completely disappears. In this episode, the guys not only break down what’s left of the special, but also wrestle with its legacy — how it became a whispered legend, a bootleg curiosity, and a rite of passage for Star Wars fans brave enough to seek it out. Was there anything worth saving? Or is its greatest contribution simply proving that even the biggest franchise in the world can spectacularly miss the mark? Strap in as the group reaches the end of the Wookiee-filled road and lives to tell the tale — barely.

What happens when a galaxy far, far away collides with late-1970s variety television and absolutely no one says no? In this very special (and possibly regrettable) episode of Surely You Can’t Be Serious, Jason and Dee are joined by special guest hosts from the 30something Movie Podcast to finally dare to watch — and break down — the now-infamous Star Wars Holiday Special. This is Part 1 of 2, and the guys go all in, dissecting every bizarre skit, every awkward musical number, every questionable story choice, and every moment that makes you ask, “How did this ever make it to air?”From uncomfortable Wookiee family dynamics, to celebrity cameos that feel like contractual obligations, to variety-show energy that completely ignores the rules of the Star Wars universe, nothing is spared. Context is provided, disbelief is shared, and sanity is repeatedly tested as the crew explores whether this special was misunderstood, doomed from the start, or exactly as bad as its reputation.Hit play and suffer joyfully with us as we document one of pop culture’s most legendary misfires — so you don’t have to watch it alone. Part 2 coming soon… assuming everyone survives.

On this episode of Surely You Can’t Be Serious, Jason and Dee dive headfirst into one of the defining albums of the 1990s: No Doubt’s Tragic Kingdom. The guys trace the band’s painfully slow rise to fame — from the Orange County ska scene and early lineup tragedy to years of label frustration — and explore how those struggles helped fuel the emergence of Gwen Stefani as a brand-new pop and alternative icon. This isn’t overnight success; it’s a hard-earned breakthrough that reshaped the sound and look of mid-’90s music.Jason and Dee break down the creation of Tragic Kingdom, its production under Matthew Wilder, and how heartbreak, ambition, and timing collided to create a cultural juggernaut. They unpack the stories behind every track, from the raw emotion of “Don’t Speak” to the attitude of “Just a Girl” and the ska-punk energy that powered the album to massive MTV and radio dominance.Over the last three weeks, the guys put Tragic Kingdom up against two other era-defining releases — Alanis Morissette’s Jagged Little Pill (Week 1) and Jewel’s Pieces of You (Week 2) — as they debate legacy, impact, and staying power. Which album truly defined the ’90s? Tune in to find out how Jason and Dee rank these iconic records.

This week on the Surely You Can’t Be Serious podcast, Jason and Dee continue their 90s album trilogy by exploring the quiet, unconventional, and deeply heartfelt debut that turned a young Alaskan singer-songwriter into a global sensation—Jewel’s Pieces of You.The guys dig into Jewel’s extraordinary backstory: her nomadic childhood in the Alaskan wilderness, the hardships that shaped her voice and worldview, and her determination to bring stripped-down, folk-driven storytelling to a pop landscape dominated by grunge and polished radio hits. Jason and Dee break down how Pieces of You was created—from the raw, minimalist production to the live-recorded tracks that captured the honesty of her coffeehouse performances.They uncover the stories behind every song, from the emotional punch of “You Were Meant for Me,” to the aching vulnerability of “Foolish Games,” to the social commentary woven throughout the album’s lesser-known tracks. And they trace the album’s slow but unstoppable rise as it connected with listeners one heart at a time, ultimately becoming one of the defining singer-songwriter albums of the decade.This is week two of a three-week showdown.  Jason and Dee kicked things off with Alanis Morissette’s Jagged Little Pill, and next week they’ll wrap up the trilogy with No Doubt’s Tragic Kingdom. Once all three albums are on the table, how will the guys rank these 90s icons in terms of songwriting, impact, longevity, and cultural footprint?Tune in to find out—because the ultimate 90s showdown is heating up.

This week on the Surely You Can’t Be Serious podcast, Jason and Dee dive headfirst into one of the defining albums of the 1990s—Alanis Morissette’s Jagged Little Pill. The guys trace Alanis’s remarkable rise from Canadian teen pop idol to alt-rock truth-teller, exploring how a young artist reinvented herself and ended up creating one of the most influential albums of the decade.Jason and Dee unpack the creation of the record—from Alanis’s fateful collaboration with producer Glen Ballard, to the raw, confessional writing sessions that would reshape her public persona and give voice to a generation. They break down the production choices that gave the album its signature emotional punch and explain how Jagged Little Pill exploded into a cultural force that no one saw coming.And of course, the guys tell the story behind every track: the heartbreaks, the therapy sessions, the studio magic, and the controversies that surrounded songs like “You Oughta Know,” “Ironic,” and “Head Over Feet.”But this is just the beginning.Over the next two weeks, Jason and Dee will compare Jagged Little Pill with Jewel’s Pieces of You and No Doubt’s Tragic Kingdom—two other iconic albums that shaped the 90s and launched careers. Which album has the strongest songwriting? The biggest cultural footprint? The deepest emotional resonance? And how will the guys ultimately rank these three 90s juggernauts?Tune in as Jason and Dee rank them all—and maybe break a few hearts along the way.