What Makes the Bill Simmons Podcast Worth Your Feed
The Bill Simmons Podcast is regularly cited as the most downloaded sports podcast of all time, growing out of Simmons’ original show, The B.S. Report, into a daily program on The Ringer.
The show mixes sports analysis with pop culture and comedy, built around a rotating cast of Ringer staffers, celebrity friends, and mainstays like Cousin Sal and Joe House.
If you are building your queue for 2026, here are ten Bill Simmons Podcast episodes worth your time.
10 Bill Simmons Podcast Episodes You Shouldn’t Miss
1. Andy Samberg on Digital Shorts and Comedy
Andy Samberg joins Simmons to discuss pioneering SNL’s digital shorts, the Rocky franchise, and hosting awards shows. It remains one of the most fondly remembered comedy crossover episodes in the catalog.
2. Nathan Fielder on the Return of Nathan For You
Comedian Nathan Fielder joins the show to discuss the return of his signature series along with a wide range of pop culture tangents. The conversation captures the show’s ability to blend deadpan comedy with genuine curiosity.
3. Charles Barkley Joins the Show
NBA legend Charles Barkley brings his outsized personality to a conversation covering basketball history and current NBA storylines. It stands out as one of the most requested guest episodes among longtime listeners.
4. Malcolm Gladwell on Ideas and Storytelling
Author Malcolm Gladwell joins Simmons for a conversation on storytelling, decision-making, and how ideas spread. It is a strong pick for listeners who enjoy the show’s occasional detours into bigger picture thinking.
5. Chuck Klosterman on Pop Culture Theory
Author and essayist Chuck Klosterman brings his signature take on pop culture and sports to a wide-ranging conversation with Simmons. Their recurring dynamic has made Klosterman one of the show’s most popular guests over the years.
6. Zach Lowe on NBA All-Star Snubs
ESPN’s Zach Lowe joins Simmons to break down All-Star snubs, the most entertaining teams to watch, and top crunch time players. It is a go-to episode for hardcore NBA fans during awards season.
7. The NBA Over-Under Mega Preview
Simmons is joined by Ryen Russillo and Joe House for the show’s annual tradition of picking win totals for every NBA team ahead of the season. It is a fan-favorite recurring format that generates some of the show’s liveliest debates.
8. The Annual My Guy Fantasy Football Draft
Simmons and a rotating group of Ringer staffers hold their yearly fantasy football draft live, mixing strategy talk with plenty of trash talk. It has become one of the show’s most anticipated seasonal traditions.
9. David Stern on the State of the NBA
In an episode dating back to the show’s earlier years, former NBA commissioner David Stern joins Simmons for a rare conversation about league business and history. It offers a different tone from the show’s usual pop culture-leaning episodes.
10. The Ringer 107 NFL Picks Tradition
Simmons and Joe Hauschka break down the week’s NFL action before making their picks for The Ringer’s long-running prediction contest. It is a good entry point for listeners who want a regular dose of football analysis alongside the banter.
Why These Episodes Stand Out in the Catalog
Each entry on this list reflects a different side of the Bill Simmons Podcast. Some bring in major comedians and authors for wide-ranging conversations, others lean into recurring sports traditions fans look forward to every year, and a few offer a rare look at league business through figures like David Stern.
That range is part of why the show has held its spot at the top of the sports podcast charts for so long.
How to Start Listening to the Bill Simmons Podcast in 2026
New episodes are published several times a week on Apple Podcasts, Spotify, and other major platforms, with video versions available on YouTube. Starting with a comedy crossover episode is a good way to sample the show’s range before following its regular sports coverage.
Frequently Asked Questions
Is the Bill Simmons Podcast only about sports?
No. While sports analysis is a core focus, the show regularly features comedians, authors, and entertainers for conversations well outside the sports world.
How often does the Bill Simmons Podcast release new episodes?
New episodes are released several times a week, with additional bonus content around major sports events and awards shows.
Where can I listen to the Bill Simmons Podcast?
The show is available on Apple Podcasts, Spotify, and other major podcast platforms, with video versions posted on YouTube.
Final Thoughts
The Bill Simmons Podcast built its audience on sharp sports analysis paired with genuine chemistry between Simmons and his rotating cast of guests.
From comedy crossovers with Andy Samberg and Nathan Fielder to annual traditions like the fantasy football draft, these ten episodes offer a strong cross-section of the show heading into 2026.
