Podcast Summary: The Lonely Island and Seth Meyers Podcast – Episode: "Like a Boss"

Release Date: June 17, 2025

Introduction

In the episode titled "Like a Boss," hosts Seth Meyers and The Lonely Island (Andy Samberg, Akiva Schaffer, and Yoram Bauman) delve deep into the creation, reception, and enduring legacy of their iconic SNL Digital Short, "Like a Boss." This episode serves as a nostalgic trip down memory lane, offering listeners an insider’s view of the creative processes behind some of their most beloved sketches and the impact they've had on popular culture.

Revisiting "Like a Boss"

Creation and Inspiration

The conversation begins with Seth Meyers expressing surprise at the massive success of "Like a Boss." Akiva Schaffer recalls how the idea originated from listening to their own music album, leading them to create a music video inspired by the phrase "Like a Boss." Andy Samberg shares:

"I don't think we thought it was going to be a hit. It was just a fun, stupid throwaway idea." (27:05)

Initial Reception

Yoram Bauman reflects on the initial response:

"When it first aired, it was funny, but I didn't expect it to become such a cultural phenomenon." (45:00)

The group discusses their low expectations and how internal enthusiasm from their record label, particularly feedback from younger colleagues, pivoted their perspective on the sketch's potential.

Unexpected Success and Legacy

The hosts are astonished by how "Like a Boss" transcended its original context to become a ubiquitous meme and a staple phrase in internet culture. Seth Meyers notes:

"I remember driving to LAX and seeing a huge billboard that was like, 'Fly Like a Boss,' and being like, whoa, there's a lot of that happening." (46:27)

Akiva adds:

"We certainly popularized the phrase after it was already somewhat prevalent, blending our comedic touch with existing cultural trends." (46:58)

The sketch's influence extends beyond SNL, inspiring various brands and media to adopt the "Like a Boss" motif, solidifying its place in pop culture.

Behind-the-Scenes SNL Stories

Phil Himes Anecdotes

Yoram Bauman shares humorous stories about Phil Himes, the longtime lighting director for SNL:

"He was super mad when we added a window for comedic effect in the Oval Office sketch. He literally walked out and confronted us about it." (05:56)

Seth Meyers humorously recounts:

"Phil Himes was like, 'There's no window there,' and I was like, 'Film buddy.'" (06:03)

These anecdotes highlight the collaborative yet sometimes challenging environment of SNL, where creative liberties often led to memorable behind-the-scenes moments.

Other Memorable Sketches

The hosts reminisce about various other sketches, such as "Hawaiian Hotel" and "To the Lighthouse," discussing the creative decisions and unexpected comedic elements that made these sketches stand out.

Akiva Schaffer describes "Hawaiian Hotel":

"Fred and Dwayne would dance around being super mean to tourists, then switch to a light, frothy Hawaiian song. It was a big laugh every time they danced off." (08:13)

Yoram adds details about "To the Lighthouse," emphasizing its intricate humor and the rapid-fire jokes embedded within the sketch.

Impact and Cultural References

Meme Culture and Brand Adoption

"Like a Boss" quickly became a viral sensation, inspiring countless memes, advertisements, and even a movie titled "Like a Boss." The group discusses how businesses like Beats by Dre and Kmart adopted the phrase for their campaigns, reflecting the sketch's widespread appeal.

Akiva points out:

"There was an Acura ad from 2015 titled 'Like a Boss,' showing how the phrase permeated various facets of media and advertising." (49:09)

Tour Experiences

Andy Samberg and Akiva Schaffer share amusing stories from their tours, where performing "Like a Boss" became a highlight for both performers and audiences alike.

"We would pass each other on stage during performances, both of us shouting 'Like a Boss.' It was a fun part of the shows." (47:27)

Yoram complements these memories by recalling the camaraderie and shared joy among the cast during live performances.

Reflections on SNL and Friendship

Throughout the episode, the hosts emphasize the enduring friendships forged during their time at SNL. They reflect on the collaborative spirit, the highs and lows of live television, and the creative bonds that have sustained them beyond the show.

Andy Samberg muses:

"Spending all that time together on tour strengthened our friendship. It's nice to have something that brings us all together even after the show." (47:41)

Yoram adds:

"We’ve been friends since we were 12, and being on stage together as part of SNL was a continuation of that lifelong bond." (47:41)

Conclusion

In "Like a Boss," Seth Meyers and The Lonely Island offer a comprehensive look into one of their most successful and culturally impactful SNL Digital Shorts. Through engaging anecdotes, reflective insights, and shared laughter, they celebrate the creativity, resilience, and friendship that defined their collaborative journey. This episode not only commemorates the success of "Like a Boss" but also underscores the lasting legacy of their contributions to comedy and music.

Notable Quotes with Timestamps

• Andy Samberg: "I don't think we thought it was going to be a hit. It was just a fun, stupid throwaway idea." (27:05)

• Yoram Bauman: "When it first aired, it was funny, but I didn't expect it to become such a cultural phenomenon." (45:00)

• Seth Meyers: "I remember driving to LAX and seeing a huge billboard that was like, 'Fly Like a Boss,' and being like, whoa, there's a lot of that happening." (46:27)

• Akiva Schaffer: "We certainly popularized the phrase after it was already somewhat prevalent, blending our comedic touch with existing cultural trends." (46:58)

• Yoram Bauman: "He was super mad when we added a window for comedic effect in the Oval Office sketch. He literally walked out and confronted us about it." (05:56)

• Seth Meyers: "Phil Himes was like, 'There's no window there,' and I was like, 'Film buddy.'" (06:03)

This episode serves as a testament to The Lonely Island's and Seth Meyers' enduring influence on comedy and their ability to create content that resonates across generations. "Like a Boss" remains a shining example of their innovative spirit and collaborative genius.