Best Pod Outcasts Podcasts (2025)

1
Tara Palmeri on Epstein and His Survivors 53:11

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16d ago53:11

53:11

This week, Larry is joined by investigative journalist, author, and podcast host Tara Palmeri to sift through the complexities of the Epstein files and his survivors—just days after several of his accusers traveled to Capitol Hill to demand accountability (1:26). They explore the confusion surrounding the case, the role of money, and how Epstein se…

1
Smurfs, Tariffs, and Our Friend from Texas 3:21:46

17d ago3:21:46

3:21:46

📌 Our guest, Bobby Vickers joins the conversation at 1:37:27 We’re back after a long stretch. The last episode came out in March, and since then it’s been tough not only to stay consistent but to bring in guests who don’t just echo our own worldview. Episode 5 was recorded on April 2nd, the day after Trump’s so-called “Liberation Day.” What began a…

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Christopher Jackson on the 10-Year Anniversary of 'Hamilton,' His Return to Broadway, and More 1:09:17

28d ago1:09:17

1:09:17

Larry is joined by Tony Award–nominated actor, Grammy- and Emmy-winning songwriter, and composer Christopher Jackson. Jackson reflects on the 10-year anniversary of ‘Hamilton,’ how the show came to life, and his experience originating the role of George Washington (2:20). He discusses his upcoming musical, 'The Crossover'; his process of writing fo…

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Wendy Lobel on ‘Anxiety Club’ 55:44

1M ago55:44

55:44

Larry is joined by Emmy Award-winning producer Wendy Lobel to discuss her directorial debut film ‘Anxiety Club’, currently streaming on Jolt.film. They begin their conversation by talking about why Wendy wanted to make the documentary and exploring the ways that the standup comedians featured in the film use their craft as built-in therapy. This le…

1
Jonathan Mahler on ‘The Gods of New York: Egotists, Idealists, Opportunists, and the Birth of the Modern City: 1986-1990’ 54:38

1M ago54:38

54:38

Larry is joined by New York Times journalist and author Jonathan Mahler to discuss his newest book, ‘The Gods of New York: Egotists, Idealists, Opportunists, and the Birth of the Modern City: 1986-1990,’ publishing on August 12. They begin their conversation by detailing why Jonathan decided to write the book and shining a light on the rich history…

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Maya Lau on ‘Easy Money: The Charles Ponzi Story’ 1:05:33

2M ago1:05:33

1:05:33

Larry is joined by journalist Maya Lau to discuss her latest podcast, Easy Money: The Charles Ponzi Story, currently streaming on Apple Podcasts. They begin their conversation by describing the story and subsequent legacy of Charles Ponzi, an Italian immigrant who, in 1920, defrauded his "investors" of the modern equivalent of a quarter of a billio…

1
Nate Jackson on 'Nate Jackson: Super Funny' 1:16:39

2M ago1:16:39

1:16:39

Larry is joined by comedian Nate Jackson to talk about his new Netflix special ‘Nate Jackson: Super Funny’. They begin their conversation by examining the different ways that comedians develop relationships with an audience and sharing how they each mentally process jokes while they're performing. Nate then details how he became a comedian and the …

1
Elizabeth Wagmeister on the Diddy Trial 52:30

3M ago52:30

52:30

Larry is joined by reporter and journalist Elizabeth Wagmeister to talk about her experiences covering the Sean ‘Diddy’ Combs federal criminal case for CNN. They begin their conversation by shining a light on the atmosphere both inside and outside the courtroom, and detailing the individual charges being brought against Combs. They then examine the…

1
Alex Thompson on ‘Original Sin: President Biden’s Decline, Its Cover-Up, and His Disastrous Choice to Run Again’ 1:01:18

3M ago1:01:18

1:01:18

Larry is joined by journalist Alex Thompson from Axios to discuss the new book he coauthored with CNN’s Jake Tapper, ‘Original Sin: President Biden’s Decline, It’s Cover-Up, and His Disastrous Choice to Run Again.’ They begin their conversation by analyzing the personal history between Joe Biden and Barack Obama and breaking down how the elements o…

1
Joy Reid on 'The Joy Reid Show' 54:26

4M ago54:26

54:26

Larry is joined by author, television host, and political commentator Joy Reid to discuss her new podcast, The Joy Reid Show. They begin their conversation by talking about why Joy left MSNBC and examining the state of cable news in modern culture. This leads to an analysis of the different ideological splits within the Republican Party and the cur…

1
Mark Whitaker on ‘The Afterlife of Malcolm X: An Outcast Turned Icon’s Enduring Impact on America’ 1:09:05

4M ago1:09:05

1:09:05

Larry is joined by writer and media executive Mark Whitaker to discuss his newest book ‘The Afterlife of Malcolm X: An Outcast Turned Icon’s Enduring Impact on America’. They begin their conversation by talking about what inspired Mark to write the book and detailing Malcolm X’s Shakespearean life journey from harrowing childhood to celebrated civi…

1
Larry Wilmore on the Trump Administration, Pope Leo XIV, the State of Hollywood, and More 1:02:49

5M ago1:02:49

1:02:49

Larry starts off a special listener mailbag episode by sharing some of his biggest concerns with Donald Trump’s second term so far and his administration’s attack on government agencies and the Constitution. Next, he talks about the brand-new Pope Leo XIV and the role of religion in modern society (22:23). After the break, Larry discusses the futur…

1
Leah Litman on ‘Lawless: How the Supreme Court Runs on Conservative Grievance, Fringe Theories, and Bad Vibes’ 1:01:23

5M ago1:01:23

1:01:23

Larry is joined by professor of law at the University of Michigan Law School and co-host of the podcast ‘Strict Scrutiny’, Leah Litman, to discuss her forthcoming book ‘Lawless: How the Supreme Court Runs on Conservative Grievance, Fringe Theories, and Bad Vibes’, publishing on May 13th. They begin their conversation by talking about how the politi…

1
Daniel Lubetzky on the Builders Movement, ‘Shark Tank,’ Kind LLC, and More 1:06:16

5M ago1:06:16

1:06:16

Larry is joined by billionaire entrepreneur and ‘Shark Tank’ costar Daniel Lubetzky, and they begin their conversation by analyzing the importance of independent thought in today’s political climate. They then focus on the objectives of the Builders Movement and Daniel's efforts to curb political extremism and heal divisions within the business com…

1
Tara Palmeri on ‘Somebody’s Gotta Win’ and ‘The Red Letter’ 59:02

6M ago59:02

59:02

Larry is joined by political journalist Tara Palmeri, writer of ‘The Red Letter’ Substack and host of The Ringer podcast ‘Somebody’s Gotta Win’, to discuss all of the latest buzz shaking up Washington D.C. They begin their conversation by analyzing the possible political repercussions of Trump’s new tariffs. This leads into a talk about the viabili…

1
Alex Isenstadt on ‘Revenge: The Inside Story of Trump's Return to Power’ 57:25

6M ago57:25

57:25

Larry is joined by Axios Senior Political Reporter Alex Isenstadt to talk about his new book ‘Revenge: The Inside Story of Trump’s Return to Power’. They begin their conversation by discussing Alex’s approach to writing the book and the environment surrounding Trump when he decided to run for president a second time. They then analyze the personali…

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Krys Marshall on ‘Paradise’ 1:11:54

6M ago1:11:54

1:11:54

Larry is joined by actress Krys Marshall to talk about the Season 2 release of her Hulu show ‘Paradise’. They begin their conversation by examining Marshall’s upbringing and the many factors that inspired her to become an actor. This leads to a conversation about the mental, interpersonal, and familial hurdles Krys overcame to reach her personal go…

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God, Guilt, and What the Hell Comes Next 1:35:39

6M ago1:35:39

1:35:39

In a world where religion has done as much harm as good, what does faith even mean anymore? In this episode, we talk with Tona Rowett and Michelle Scott-Huffman about what happens when belief gets messy, and how people are reclaiming spiritual identity after trauma. We get into the damage done by the Church, the quiet power of personal theology, an…

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National Divorce: A Bad Idea, or Inevitable? | Elijah Haahr 2:13:34

7M ago2:13:34

2:13:34

In this episode of Middle Outcast, we talk with Elijah Haahr, former Speaker of the Missouri House of Representatives, about the shifting landscape of American politics. We discuss how long-form conversations are changing political engagement, the role of social media in deepening polarization, and whether the United States is truly headed for a na…

1
George & Teddy Kunhardt on ‘Becoming Katharine Graham’ 1:03:31

7M ago1:03:31

1:03:31

Larry is joined by filmmakers George and Teddy Kunhardt to discuss their newest documentary ‘Becoming Katharine Graham’, currently streaming on Amazon Prime Video. They begin their conversation by talking about what inspired them to start the project and shining a light on the male-dominated world Katharine lived in when she was running the Washing…

1
Thomas Chatterton Williams on "How the Woke Right Replaced the Woke Left" 1:05:28

7M ago1:05:28

1:05:28

Larry is joined by writer and cultural critic Thomas Chatterton Williams to discuss his latest essay for The Atlantic, "How the Woke Right Replaced the Woke Left". They begin by shining a light on the political left’s weak hold on the cultural landscape, and breaking down the definition, history, and downfall of "woke" ideology. Next, they take a l…

1
Roy Wood Jr. on ‘Lonely Flowers’ and ‘Have I Got News for You’ 1:04:27

8M ago1:04:27

1:04:27

Larry is joined by actor and comedian Roy Wood Jr. and they begin their conversation by acknowledging Black History Month. Roy then breaks down his new CNN show ‘Have I Got News for You’ and opines on whether or not comedic "bubbles" will last under the new Trump administration (5:41). They then pivot to his recently released stand-up special on Hu…

1
Who? 32:46

8M ago32:46

32:46

In this episode of Middle Outcast, we take a step back and introduce ourselves—Tom and Myke—and share the stories that shaped who we are today. From Myke's journey as a Midwest tinkerer turned community-building tech guru to Tom’s path from a small-town kid to a Marine Corps veteran with a passion for creating and problem-solving, we explore the un…

1
Juanita Tolliver on ‘A More Perfect Party: The Night Shirley Chisholm and Diahann Carroll Reshaped Politics’ 59:09

8M ago59:09

59:09

Larry is joined by journalist and MSNBC political analyst Juanita Tolliver to discuss her new book, ‘A More Perfect Party: The Night Shirley Chisholm and Diahann Carroll Reshaped Politics’. They begin their conversation by talking about what inspired Tolliver to write about the legendary political fundraiser and shining a light on the many influent…

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Laura Coates on ‘Laura Coates Live’ 1:04:29

8M ago1:04:29

1:04:29

Larry is joined by CNN Anchor and Chief Legal Analyst Laura Coates, and they begin their conversation by talking about Laura’s stylistic approach to the interviews she conducts on her show ‘Laura Coates Live’. They then break down the defamation case between ABC News and Donald Trump and discuss the reasons why there is currently a general mistrust…

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RaMell Ross on ‘Nickel Boys’ 1:07:53

8M ago1:07:53

1:07:53

Larry weighs in on the L.A. fires. He’s then joined by writer and Academy Award-winning filmmaker RaMell Ross to discuss his newest movie ‘Nickel Boys ’(8:33). They begin their conversation by talking about how the project came together, RaMell's experimental inspirations, and the screenwriting process with co-writer Joslyn Barnes. Next, they dive …

1
New Year New Pod 26:22

9M ago26:22

26:22

In the inaugural episode of Middle Outcast, hosts Myke and Tom set the stage for their ambitious mission to foster real conversations in a fractured world. They discuss the challenges of polarization, the harm of “memeification,” and the power of honest dialogue in bridging ideological divides. With humor, humility, and a vision for connection, the…

1
Alan Zweibel on the Early Days of ‘Saturday Night Live’ 1:03:50

9M ago1:03:50

1:03:50

Larry is joined by Emmy Award-winning writer and producer Alan Zweibel to discuss his experiences working on ‘Saturday Night Live’ during its first few years on the air. Alan begins the conversation by sharing his feelings about the 50th anniversary of ‘SNL’ and detailing the anatomy of a good joke. Larry and Alan then talk about Lorne Michaels’s o…

1
Emily Chang on ‘Posthuman’ and ‘The Circuit’ 54:17

10M ago54:17

54:17

Larry is joined by technology journalist Emily Chang to talk about her Bloomberg Originals limited series ‘Posthuman’, and her podcast ‘The Circuit’, which features interviews with influential figures in the tech industry. They begin their conversation by discussing the inspiration for ‘Posthuman’, which delves into humanity’s connection to artific…

1
Timothy Shenk on ‘Left Adrift: What Happened to Liberal Politics’ 1:09:09

10M ago1:09:09

1:09:09

Larry is joined by writer and historian Timothy Shenk to discuss his newest book, ‘Left Adrift: What Happened to Liberal Politics’. They begin their conversation by talking about why they think the Democrats failed with their messaging in the 2024 election and what the rise of Trumpism means about American culture today. Next, Shenk shares the hist…

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S.E. Cupp on ‘Off the Cupp’ 1:24:02

10M ago1:24:02

1:24:02

Larry weighs in on the results of the presidential election and the future of the Democratic Party. He’s then joined by political commentator and host of the new iHeartRadio podcast ‘Off the Cupp’, S.E. Cupp, and they begin their conversation by sharing their reactions to Donald Trump winning the presidential election (18:01). They then examine the…

1
Samantha Bee and Joanna Coles on ‘The Daily Beast Podcast’ 1:00:25

11M ago1:00:25

1:00:25

Larry is joined by comedian Samantha Bee and chief content officer at The Daily Beast, Joanna Coles, to discuss their latest venture ‘The Daily Beast Podcast’. They begin their conversation by shining a light on how they started the podcast and the interesting way Joanna connects creative luminaries in her industry. They then quickly pivot to an ex…

1
Craig Unger on ‘Den of Spies: Reagan, Carter, and the Secret History of the Treason That Stole the White House’ 59:38

11M ago59:38

59:38

Larry is joined by journalist and writer Craig Unger to discuss his newest book ‘Den of Spies: Reagan, Carter, and the Secret History of the Treason That Stole the White House’, which investigates the secret collusion between the U.S. government and Iran and how it affected the 1980 presidential election. They begin the pod by diving into the histo…

1
Nate Silver on “On the Edge: The Art of Risking Everything” 1:21:07

11M ago1:21:07

1:21:07

Larry weighs in on his recent tour, the newest season of ‘Reasonable Doubt’, and the upcoming presidential election. He’s then joined by writer, statistician, and founder of the site FiveThirtyEight Nate Silver to discuss his newest book ‘On the Edge: The Art of Risking Everything’ (15:27). They begin their conversation by talking about why certain…

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Yuval Noah Harari on ‘Nexus: A Brief History of Information Networks from the Stone Age to AI’ 1:28:53

12M ago1:28:53

1:28:53

Larry is joined by historian and author Yuval Noah Harari in front of an audience at Live Talks L.A. to discuss his newest book, ‘Nexus: A Brief History of Information Networks From the Stone Age to AI.’ They begin their conversation by talking about the nature of information and how it's been manipulated throughout human history, starting with the…

1
Abby Phillip on ‘NewsNight with Abby Phillip’ 57:52

1y ago57:52

57:52

Larry is joined by journalist and host of CNN’s ‘NewsNight’, Abby Phillip, and they begin their conversation by discussing Donald Trump and his influence on the news media and the Republican Party. They then pivot to Kamala Harris and shine a light on her meteoric rise to the top of the Democratic ticket and break down the effectiveness of her medi…

1
Will Packer on ‘Fight Night: The Million Dollar Heist’ 1:17:19

1y ago1:17:19

1:17:19

Larry weighs in on the debate between Donald Trump and Kamala Harris. He’s then joined by producer Will Packer to discuss his new Peacock limited series ‘Fight Night: The Million Dollar Heist’. They begin their conversation by discussing the premise and history behind the project, which leads to a discussion about the art of creating content in tod…

1
Sophia Cai on the DNC 1:11:48

1y ago1:11:48

1:11:48

Larry weighs in on the state of the presidential race and shares some of dates of his upcoming tour. He’s then joined by Sophia Cai from Axios and they begin their conversation by talking about Kamala Harris’s historic rise to Democratic presidential nominee and the change in party dynamics after Joe Biden dropped out of the race. They then examine…

1
Langston Kerman on ‘Bad Poetry’ 1:08:52

1y ago1:08:52

1:08:52

Larry is joined by actor, writer, and comedian Langston Kerman to talk about his brand new Netflix stand-up comedy special ‘Bad Poetry’, streaming on Aug. 20th. They begin their conversation by breaking down different types of comedy writing and examining Langston’s process when coming up with themes for a special. This leads to discussions about d…

1
Marion Jones on the Olympics and Driven Inc. 1:08:14

1y ago1:08:14

1:08:14

Larry weighs in on his favorite moments from the 2024 Olympics so far, Tim Walz, Trump’s wild press conference, and the state of Kamala Harris’s presidential campaign. He’s then joined by former world champion track-and-field athlete Marion Jones and they begin their conversation by discussing her journey from teenage phenom athlete to a star on th…

1
Governor Wes Moore on the Democratic Party and Kamala Harris 46:28

1y ago46:28

46:28

Larry weighs in on this week’s attacks against Kamala Harris by the right-wing media. He’s then joined by Maryland Governor Wes Moore and they begin their conversation by discussing the many accomplishments Moore has achieved for his state, and the general mood of the Democratic Party after Joe Biden dropped out of the race and Kamala Harris steppe…

1
Scott Galloway on ‘The Algebra of Wealth’ 1:23:47

1y ago1:23:47

1:23:47

Larry weighs in on Joe Biden dropping out of the presidential race. He’s then joined by professor, author, and entrepreneur Scott Galloway; they begin their conversation by discussing the art of doing interviews, the state of mainstream TV as a viable information source, and the schism between left and right political ideologies (16:47). They then …

1
Episode 15 - 1st LT M.G.H 33:59

1y ago33:59

33:59

In today's episode, we explore the extraordinary wartime odyssey of 1st Lt. M.G.H., a B-24 pilot serving with the renowned 307th Bomb Group during World War II. Through a poignant letter written to his brother, M.G.H. vividly recounts a pivotal mission over the Philippines in 1944. The narrative unfolds with gripping detail as M.G.H. describes the …

1
Colman Domingo on ‘Sing Sing’ 58:21

1y ago58:21

58:21

Larry weighs in on President Joe Biden. He’s then joined by director, playwright, and Emmy Award-winning actor Colman Domingo to discuss his latest film ‘Sing Sing’ (13:55). They begin their conversation by talking about the process of choosing roles for a project and describing the premise of ‘Sing Sing’, which centers around a group of prison inm…

1
Episode 14 20:35

1y ago20:35

20:35

In this episode we have a few awesome stories! In our first story a Female Helicopter Pilot saves the day after a catastrophic Engine Malfunction Then a US Marine maliciously complies while testing an experimental Weapons System! How a road in an Australian Army Training Base got it's nickname And finally, how some studious Marines find a way to sn…

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Episode 13 28:18

1y ago28:18

28:18

This episode features three longer stories, starting with Pilgorepax's tale about his great-great-grandfather from Ontario, Canada. His ancestor was pulled out of a Montana state prison in 1916 for accessory to murder and enlisted in the 113th Lethbridge Highlander battalion in Alberta. Despite numerous challenges, including injury and frequent inf…

1
Episode 12 24:29

1y ago24:29

24:29

We’re back! After a long hiatus, sharing military anecdotes from various listeners. We just want to advise too that this episode needs a trigger warning, as it does involve a death. The first story is from Duck Force One, recounting an incident where a tiny Indian conscript driving an XO's car in a convoy was hit by another car, leading to a humoro…

1
Bill Maher on 'What This Comedian Said Will Shock You' 1:21:37

1+ y ago1:21:37

1:21:37

Larry is joined by comedian Bill Maher in front of a live audience at Live Talks L.A. to discuss his new book 'What This Comedian Said Will Shock You'. They begin by shining a light on how Bill compiled his favorite editorials from ‘Real Time with Bill Maher’ for the book and contrasting the focus of the hit HBO series with the celebrity-formatted …

1
Janine Sherman Barrois on ‘The Big Cigar’ 57:39

1+ y ago57:39

57:39

Larry is joined by writer, producer, and showrunner Janine Sherman Barrois to discuss her latest venture ‘The Big Cigar’ currently streaming on Apple TV+. They begin their conversation by discussing the difficulties of making a genuine high-budget biopic that features such a polarizing cultural icon like Huey Newton. Janine then shares what she lea…

1
Stephen Merchant on ‘The Outlaws’ 1:02:31

1+ y ago1:02:31

1:02:31

Larry is joined by actor and comedian Stephen Merchant and they begin their conversation by comparing the American and British versions of ‘The Office’, and sharing stories from making their respective iterations of the hit TV show. They then pivot to the Amazon Prime series ‘The Outlaws’ which recently premiered its third season and features Merch…