Podcast Summary: The Al Franken Podcast
Episode: BEST OF: Jimmy Kimmel on His Career in Comedy!
Release Date: December 28, 2025
Guest: Jimmy Kimmel
Host: Al Franken
Episode Overview
This special “Best Of” episode features a 2020 conversation between Al Franken and late night host Jimmy Kimmel, focusing on Kimmel's journey in comedy, his background in radio, the evolution of "Jimmy Kimmel Live," and the intersection between comedy and politics—especially how Kimmel’s personal experiences brought him into the public healthcare debate. The discussion ranges from the challenges of making late night television, reflections on the changing political climate, behind-the-scenes tales of booking guests, advice for aspiring comedy writers, and Kimmel's thoughts on hosting the Oscars. The episode is peppered with candid and funny moments, giving listeners a window into the realities of comedic success, public responsibility, and the enduring value of humor.
Key Discussion Points & Insights
1. Jimmy Kimmel’s Radio Roots and Early Comedy Influences
[05:19–08:17]
- Kimmel started in radio while still in college and spent over a decade as a morning show host, learning to love the long-format medium.
- He describes the “luxury” disc jockeys feel hearing their own voice on the microphone, and how the ability to “talk over the music intro” was coveted for more airtime.
- Radio, he notes, taught him the skills of keeping an audience engaged in real-time and the importance of stretching content.
"Most disc jockeys… they wind up speaking like something other than a human being because they’re listening too closely to their own voice."
— Jimmy Kimmel [05:41]
2. The Evolution and Challenges of "Jimmy Kimmel Live"
[09:39–13:30, 26:02–34:57]
- The show's early years were described as “a mess”—a lack of guest interest, inexperience among staff, and Kimmel's naive belief he could radically reinvent the late-night format.
- Frequent guest shortages led him to rely on comedians like Sarah Silverman and Adam Carolla.
- Kimmel discusses TV audience expectations and learning the “hard lesson” that while you can innovate on late night, you can’t abandon the core format entirely.
“That was my first big mistake: I was so focused on making the show different, I didn’t focus on making it good.”
— Jimmy Kimmel [32:07]
- Over time, the show developed its character through recurring comedy bits and loyal writing staff, slowly building stability and confidence.
“Those… go to comedy bits… are like the buoys you can cling on to. If you don’t have those things, you’re just paddling for your life.”
— Jimmy Kimmel [33:51]
3. Guest Selection, the Art of Interviewing, and Celebrity Interactions
[08:50–10:58; 51:31–54:16]
- Kimmel outlines the difference between good and bad guests: Good guests expand on questions; bad ones are “great at depositions.”
- He’s “super interested in people and the specifics of their jobs,” often engaging with audience members about their lives off-camera, which Franken points out makes him an empathetic interviewer.
- The hazards of booking: Early on, he sometimes didn’t even have a guest for the night’s taping.
- Tales from co-hosting experiments (Monica Lewinsky, Mike Tyson) and instances where the guest would refuse to discuss expected topics.
“I am super interested in people and their jobs and the specifics of their jobs.”
— Jimmy Kimmel [51:39]
4. Comedy and Politics: Personal and Societal Impact
[13:34–23:32; 42:01–44:50; 63:38–64:20]
- Early in his late-night career, Kimmel intentionally avoided overtly political or serious content, preferring to lampoon the “silly stuff.”
- The birth of his son, Billy, with a congenital heart condition, transformed his civic perspective. His emotional monologue about healthcare solidified his participation in the public policy debate, especially around the Affordable Care Act.
"It just hit me like, wow, this is such a burden on these people... Could you imagine if this hospital wasn’t here to pay their medical bills? ...I do try to, when something bad happens to me... at least I have a funny story; at least I have something I can talk about on the air."
— Jimmy Kimmel [15:31]
- Franken credits Kimmel’s “raw humanity” with influencing the national debate about healthcare, especially regarding pre-existing conditions.
- Both express frustration with the current divisiveness, and share skepticism for abolishing private insurance in universal healthcare.
“This idea… 150 million Americans have private insurance, and a lot of them really like their private insurance.”
— Al Franken [22:00]
5. Behind the Curtain: Writing for Late Night and the State of Comedy
[34:57–41:11]
- Kimmel and Franken swap philosophies on how to choose writers—original voice vs. formula fulfillment.
- They bemoan the new “track” of professional comedy writing, compared to when only innately funny people gravitated to the work.
- Kimmel values perspective: “Would I put this on the air?” is his sieve for writers’ submissions.
- Both dislike that comedy writing is now seen as just a “job,” with some people in it who simply “figured out how to be funny enough to fake it.”
“Some of the people that work on my show are just the funniest person in almost every room they’re in… And you can’t teach that.”
— Jimmy Kimmel [38:31]
6. Career Commitment, Persistence, and the Necessity of Comedy
[41:12–45:00]
- Discussing the necessity of truly “having to be a comedian” (quoting Dana Carvey).
- Kimmel recounts being fired repeatedly from radio jobs across the country, supporting a young family, and never seriously considering a Plan B.
“There is no Plan B. There is just this plan.”
— Jimmy Kimmel [43:03]
- He acknowledges the “preposterous” nature of comedians’ pay compared to other professions, showing gratitude for the work but awareness of its privileged status.
7. Late Night Landscape, Late Show History, and the Oscars
[25:54–34:57; 57:12–60:20]
- Kimmel reflects on the evolution from the era of a single late-night king (Carson) to a more competitive and crowded market.
- The stress of the early years gives way to confidence and gratitude for being allowed to grow the show.
- On hosting the Oscars: He saw it as a major milestone, focusing on jokes but ensuring unscripted moments could still happen (e.g., tour bus and movie theater surprises, Jet Ski prize for the shortest speech).
- Kimmel finds “perverse” enjoyment in the risk of bombing.
“If ever you’re going to do a lot of work, that’s the time... you don’t want to end up on a ‘worst Oscar host’ list.”
— Jimmy Kimmel [59:33]
8. Influences and Reflections on Fame
[61:12–63:56]
- Cites Letterman and Howard Stern as biggest influences, with nods to Steve Martin, Bill Murray, Richard Pryor, and even Franken (“people used to call me Al Franken all the time” [61:36]).
- Kimmel recalls personal highlights, like learning Richard Pryor was a fan of one of his shows.
- Observes that fame doesn’t always transfer into political awareness: even top figures like Mike Bloomberg sometimes don’t recognize him.
Notable Quotes & Memorable Moments
-
On the grind of late night:
"I don’t want to do anything that I have to do. And some nights, it’s harder to do than others. And of course, the president makes it even more of a burden..."
— Jimmy Kimmel [10:36] -
On comedy as a necessity, not a choice:
“No one should be a comedian unless they have to be a comedian.” — Dana Carvey, quoted by Al Franken [42:01]
“I think so too.” — Jimmy Kimmel -
On the risk of innovation:
“I was so focused on making the show different, I didn’t focus on making it good.”
— Jimmy Kimmel [32:07] -
On the luxury and luck of being paid to be funny:
“I sometimes still look at my house and go, geez, I can’t believe they gave me this for telling jokes. It’s crazy.”
— Jimmy Kimmel [44:35] -
On the realities of comedy writing:
“There are a lot of writers that are just smart people who decided they want to be a comedy writer, and… they figured out how to be funny enough that they can kind of fake it.”
— Jimmy Kimmel [37:31] -
A moment of humility:
“The truth is, we always did pretty well in the ratings, and even though the show was genuinely terrible… We did okay in the ratings, so.”
— Jimmy Kimmel [33:10] -
On real curiosity in interviews:
“I’m super interested in people… their jobs… and I always want to know what they do and where they’re from…”
— Jimmy Kimmel [51:39]
Timestamps for Important Segments
- 05:19 — Kimmel on his radio roots and early radio lessons
- 09:39 — The woes of bad guests and importance of guest selection
- 13:34 — Avoiding politics, then the Billy healthcare story
- 15:31 — Kimmel describes his perspective in the hospital, calling for empathy in health care
- 26:02 — The history and landscape of late night TV and starting "Jimmy Kimmel Live"
- 32:07 — Lessons learned in late night: the risk of being “different”
- 34:57 — The process and philosophy of hiring comedy writers
- 41:12 — On necessity and persistence in becoming a comedian
- 43:03 — Kimmel on not having a Plan B
- 57:12 — Hosting the Oscars, approach and unique segments
- 61:12 — Biggest comedic influences and a surprising story about Richard Pryor
Overall Tone & Final Thoughts
The conversation balances insider humor, industry wisdom, political seriousness, and humility. Both Kimmel and Franken are candid and unguarded, giving listeners insight into what it really takes to succeed in comedy—and the grittier, not-so-glamorous roads that lead from local radio to the Oscars stage. There’s an undercurrent of social responsibility, especially regarding the role comedy can play in healthcare debates and public discourse. At its heart, the episode is a testament to the resilience, luck, and curiosity required to make a lasting impact in American satire and television, while never losing sight of the privilege—and responsibility—of making people laugh.
For listeners seeking laughter, industry secrets, and earnest reflections on the intersection of public life and comedy, this "Best Of" episode delivers it all.