Best Toby O Brien Podcasts (2024)

1
Actor Craig Bierko Warns Jay To Never Ride A Horse 51:51

1d ago51:51

51:51

We talked about: Finding community, doing The Stump, Not doing Chandler on “Friends”, the wonderful and difficult friendship of Matthew Perry, doing theater as a kid, “easy” comics who took their time, playing villains, lying about knowing how to ride horses and almost dying on the horse, auditioning by “being that guy” to set you apart, The Great …

1
Jim Colucci & Frank DeCaro Explain Why Jay Alienates Stars 46:40

8d ago46:40

46:40

This is our most gossipy episode ever! Jim and Frank, one of my favorite couples, spill the tea on the icons you want to know most if it were 1983. Sarah Mills, Andy Warhol, and yes, humiliating yourself in front of Merril Streep are all on topic. We discuss occasionally overstepping and finding their way to any and every premiere and the joys of b…

1
Stephen Markley, Accuses Jay Of Destroying The Earth 45:13

15d ago45:13

45:13

Novelist/Environmental Activist, Stephen Markley talked about the coming environmental disaster and other laugh out loud subjects. Stephen thinks there’s hope but mostly it’s by applying pressure to big business and government which sounded hard to Jay. We also talked about writing for ONLY MURDERS IN THE BUILDING (Jay and Stephen shared stories ab…

1
Larry Wilmore Tells Jay He’s Podcasting Wrong. 43:44

22d ago43:44

43:44

On this week’s episode the versatile writer, creator, actor, & comic Larry Wilmore talks about growing up in Pomona, CA and finding comedy and magic, hanging with President Obama. We compare notes on LA, TV, the Dodgers, SNL, Steve Martin, Eddie Murphy, losing a sibling and we challenge each other to do stand-up comedy. Bio: Emmy Award winner Larry…

1
Sklar Bros Defend Jay’s Moronic Love of Sports 45:30

29d ago45:30

45:30

Bio: Randy and Jason Sklar can currently be seen in the fourth season of FX’s WHAT WE DO IN THE SHADOWS playing fictional Property Brothers ‘Bran and Toby Daltry’. The Sklars produced, wrote, and starred in THE NOSEBLEEDS, a UFC original series that released this summer on UFC’s Fight Pass. The series is a hilarious deep dive into UFC’s history fea…

1
Conan O’Brien Explains That Jay Needs to Just Shut Up 45:32

1M ago45:32

45:32

Conan O’Brien and Jay discuss the neurotic need to constantly make jokes at the peril of personal relationships and true communication. They also talk about their kids and wives putting up with them, their long friendship, podcasting, comedy, growing older in comedy, Conan’s new show “Conan O’Brien Must Go”, and reading commercials. Bio:Conan O'Bri…

1
Weird Al Perfects His Craft While Jay Clearly Doesn't 42:53

1M ago42:53

42:53

Jay smothers Weird Al with love and appreciation for Al’s perfection in his parody. We talk about Mad Magazine, Looney Tunes, pizza, travel, doing what you want, the power of an orchestra, the two pulls of being a comic vs a musician, how a true showman can come out of Linwood, and giving up architecture for being a professional goofball/genius. Bi…

1
Tony Shalhoub Declares Jay’s Too Shallow 43:25

2M ago43:25

43:25

Tony and Jay meet for the first time. We talk about the depth of his character, Primo, in “The Big Night” and why Jay can’t find that depth in real like. We also chat about growing up the 9th of 10 kids, the acting scene in Green Bay, WI., tailoring Monk for Tony, auditioning, the struggles of being an actor, & Tony’s biggest mistake which lead to …

1
Toby Huss Explains Why Jay Can’t Handle Adventure 46:44

2M ago46:44

46:44

Toby and Jay talked about art and trying to see art (and life) from unique perspectives. Jay calls Toby a weirdo. And, like a weirdo, he accepts it as the compliment which is what it was actually meant to be. We talk about failing at school, meeting a guy called Magic who makes pipes out of antlers, and working as a janitor in a church and 10000 ot…

1
Author Kliph Nesteroff Tells Jay He's Remembering His Life Wrong 1:26:40

2M ago1:26:40

1:26:40

Entertainment Journalist and all around funny guy Kliph Nesteroff talks about a Canadian kid who got into collecting stories of strange and eccentric show business events. We both talk about our short lived stand-up days. Capturing worthwhile memories, and how Milton Berle was a jerk. I also stump Kliph when I ask him what else he would care about …

1
David Wild’s 30 Year Party With Music’s Biggest Names & Why Jay’s Not Invited 46:23

2M ago46:23

46:23

David, fresh off of a weekend with Donny Osmond talks about a lifetime of celebrities. Idolizing them, meeting them, interviewing them, befriending them and eventually making them stars once again on his grammy specials. We also talk Neil Diamond, Joni Mitchell, Frank Sinatra, and Phil Rosenthal plus a special surprise call from Brad Paisley! Bio: …

1
Writer Eugene Garcia-Cross Explains Why Jay Isn’t Happy Enough 59:12

3M ago59:12

59:12

Eugene Garcia-Cross talks about growing up in Pennsylvania, losing his dad early, and becoming a literature professeur only to give it all up to be a Hollywood comedy writer. Only to wind up writing books on the side. He also talks about struggling as a 35-year-old assistant, how to be patient for the next job. making the most out of the writers ro…

1
Singer Nicole Atkins Tells Jay He’s Been Squandering His Creativity 1:07:28

3M ago1:07:28

1:07:28

Nicole talks about the difference between creation and nervous activity and how hard it is to distinguish between the two. We also talk about procrastination, Elvis Costello, the need to let ideas simmer, collaborating on a show, making an album, the meaning of music, the tricks to productivity, and the joy of baby steps. Bio: For two decades, Nico…

1
John Ross Bowie Explains Why He Can Meet His Heroes and Jay Can’t 44:50

3M ago44:50

44:50

We talk about how to pronounce Bowie, the love of Monty Python, Elvis Costello, growing up in New York, the Ramones. John’s new play, Brushstroke, my love of John’s wife, Jamie Denbo, John’s possible love of Jay’s wife if he ever meets her, John Cleese, John’s dad who wanted to be an actor but never did it but then turned John on to great movies, t…

1
Director Paul Feig Encourages Jay To Completely Remake Himself ASAP! 46:24

3M ago46:24

46:24

Paul and Jay discuss looking like losers and feeling like winners, and wearing clothes to match your goals and garner respect, being authentic, Mt. Clemens, Michigan, directing, collaborations, why Paul prefers dinners with girls, why I’ll have to fly to London to see him again, his next movie, his wife Laurie, drinking Artingstall Gin, Paul’s “Coc…

1
Millennials Tell Jay Why The Youngs Will Never Love Him. 49:57

4M ago49:57

49:57

We talk about trying to stay positive in a down comedy market, how Jay did or didn’t fit in writing a pilot with much younger people, what started the desire to perform, inspirations, Boy Meets World, and the trick to showbiz is just never leaving. Bios: Lucy Blehar is an actor, writer, and musician from Pittsburgh, Pennsylvania (home of Heinz Ketc…

1
Writing Legend Rob Edwards Exhorts Jay To Avoid Showbiz Disaster 1:02:23

4M ago1:02:23

1:02:23

We discuss our friendship since 1985, teaching at USC, the graphic novel “Defiant” about slave Robert Smalls who stole a southern ship and gave it to the north, Rob’s analytical brain, being teamed with a monster, being fooled by a first meeting, insane show runners with guns on the table, being a black writer, the sunk cost fallacy, making The Pri…

1
Kevin Nealon Explains Why Jay’s Son Will Never Respect Jay 1:08:08

4M ago1:08:08

1:08:08

Comedian Kevin Nealon talks about being an older dad, and the butt of all jokes, bad impressions, secret to stand-up comedy, stumbling into SNL and making Weekend Update and how good Germany smells. Bio:Emmy and SAG-nominated actor, comedian, and author Kevin Nealon is best known for his nine-year stint as a cast member of NBC's Saturday Night Live…

1
Actress Suzy Nakamura Explains Why Jay’s A Hack 1:16:02

4M ago1:16:02

1:16:02

On this episode we talk about making art for artsake. Suzy convinces Jay to start a second career as an actor and demands I put myself in my own show. We also talk about Chicago, Crate and Barrel, reliving one year, old people holding tissues all the time, and the greatest show about masturbation ever created. Bio: Born and raised in Chicago, Suzy …

1
Gary Gulman Explains Why Jay’s Latchkey Childhood Ruined Him 1:15:07

4M ago1:15:07

1:15:07

Comedian/Author Gary Gulman and Jay compare their latchkey childhoods with memories of being alone, watching endless TV and worrying about whether the real world would have more channels. We also talk about needing to be funny, the excitement of being on a soundstage for the first time, how one of us was built to play basketball, and how we owe our…

1
Bryan Cranston Details Why His Life Is So Much Better Than Jay's 1:07:38

5M ago1:07:38

1:07:38

Bryan talks about commiting to craft and giving up on whether you get the gig. We compare notes about growing up in the valley without adult supervision, writing, why celebrities feel better with other celebrities, the difference between Tequila and Mezcal, having kids in the arts, getting your heart broken in 5th grade, the lessons of struggling, …

1
Rizwan Manji tells Jay to not box himself in already! 52:14

5M ago52:14

52:14

Rizwan how he got from Calgary to Hollywood, how he stopped playing terrorists and started playing himself, how serious actors who have the knack for funny can make it, and how Jay needs to reconsider acting as a profession. Bio: Rizwan Manji is one of Hollywood’s most respected TV and screen actors. He received a Best Guest Actor nomination for hi…

1
Comedy Legend Lew Schnieder Scolds Jay for Crossing The Comedy Line 1:03:51

5M ago1:03:51

1:03:51

Writer/comic Lew Schnieder and Jay talk about the jokes they aren’t allowed to tell and how important being “funny” is to them both. Bio: Lew Schneider is a youthful 62 year old man. From Straw Hut MediaBy Straw Hut Media

1
Kevin Nealon Shames Jay for Not Being A True Artist 37:04

5M ago37:04

37:04

The talented Kevin Nealon comes in for a quick visit in between painting, writing, stand up, acting and being a renaissance man, while Jay… isn’t. They discuss what’s normal and why Jay can’t be. Bio: Emmy and SAG-nominated actor, comedian, and author Kevin Nealon is best known for his nine-year stint as a cast member of NBC's Saturday Night Live, …

1
Stephen Root Tells Jay Why He’ll Never Fit In 1:02:28

5M ago1:02:28

1:02:28

Stephen Root is a genius actor who brought humanity to the character of the outsider. Jay and Stephen share the feeling of being on the outside and how that makes being an artist more insightful but being a guy at a party more of a drag. Stephen talks about the art of acting and auditioning and what it’s like to finally be able to tell the producer…

1
Andy Richter Explains Why It’s Great Jay Has No Chance At Being Famous 1:28:40

6M ago1:28:40

1:28:40

Comedian/Actor Andy Richter shares stories of fame, fans, and family and being a regular guy in an irregular world. Bio: Andy Richter has been working in television comedy for over 30 years as an actor, writer, host and producer. He’s best known as Conan O’Brien’s sidekick, but has been in numerous movies and tv series. He hosts the podcast The Thr…

1
Jamie Denbo tells Jay Why He’ll Never Get What He Wants 54:24

6M ago54:24

54:24

Funny Actress/Writer/Improviser Jamie Denbo talks about jumping in the water of acting and writing while also trying to have a decent relationship with your kids. As expected, none of it is easy but Jamie somehow makes it work. Bio: Jamie Denbo currently serves as CO-EP on the 20th season of ABC’s smash hit, Grey’s Anatomy. She was the creator, EP …

1
Singer/Songwriter, Charlie Kogen, Explains Why Jay’s A Terrible Dad 1:12:54

6M ago1:12:54

1:12:54

Jay challenges his son, college senior, Charlie Kogen, to list the top 5 things Jay did wrong (and right) as a father. Along the way they talk about pushing your kid too hard, the pain of spending time apart, fear of the future, and the tyranny of expectations. Jay explores the dichotomy between loving fatherhood and wishing he could trade it for p…

1
Lisa Kudrow Explains Jay’s Marriage To Writer, Brown Kogen 1:18:28

6M ago1:18:28

1:18:28

Lisa Kudrow helped introduce Jay to his wife Brown Mandell, and now 27 year later they are all trying to make sense of it. Brown has issues with Jay. Jay has issues with Brown and Lisa understands them both even when neither is making sense. Tune in to marriage miscommunication on this week’s DBAWJK! Bio: Lisa Kudrow. She was on Friends. Full bio o…

1
Phil Rosenthal Tells Why Jay Doesn’t Deserve Good Things 1:03:59

7M ago1:03:59

1:03:59

The great writer/actor/food & travel show host, Phil Rosenthal talks Jay down from feeling bad about undeserved success. Phil claims dumb luck is part of the game. They also talk about good times, Jack Benny, spoiled kids, great show-running, enjoying life, being able to connect with people no matter what. Bio:Phil Rosenthal is the award-winning cr…

1
Greg Grunberg Rescues Jay From The Loneliness of Modern Life 58:23

7M ago58:23

58:23

In one of our first recordings, Actor, writer, director, and all around mensh, Greg Grunberg helps Jay settle in on what podcasting is and how it might help get people (and especially kids) more connected in their ever increasingly isolated life. And if we can’t fix that, then maybe, just maybe, we can sell them stuff. Bio: Actor/Producer and epile…

1
Richard Kind Explains Why He’s Allowed To Say Anything He Wants and Jay Isn’t 1:29:12

7M ago1:29:12

1:29:12

Character actor extraordinaire, Richard Kind, talks about having the authenticity and self confidence to speak his mind and get away with it. He says having a healthy ego and approaching the world with joy give him permission to say just about anything. And how that confidence goes into his landing acting jobs and parenting his children. We also ta…

1
Dave Foley Tells Jay About UFO’s, Friendship, Comedy and Other Mysteries 1:10:54

7M ago1:10:54

1:10:54

Comedy hero and one of Jay’s best friends helps Jay work though the deep mysteries of friendship, UFO’s, their failed hit movie “The Wrong Guy” and how to stay pals for 30 years. Bio: Dave Foley rose to fame as “the cute” member of the revered sketch group, “Kids In The Hall”. He went on to star in “News Radio” and dozens of movies and TV shows, He…

1
Dana Gould Talks About Jay’s Newfound Irrelevance 1:04:19

8M ago1:04:19

1:04:19

Dana talks to Jay about the ego death of change. You think you’re something and then you’re not. He talks about aging, dadding, growing comfortable with being who is and being damn lucky to be that. Bio: Dana Gould began his professional comedy career at the age of seventeen with six solo stand-up comedy specials and done all talk shows from LETTER…

1
Actor Kevin Pollak Explains to Jay Why Irresponsible Gambling Makes Sense 1:27:29

8M ago1:27:29

1:27:29

The brilliant Kevin Pollak forgives Jay for being late, talks about poker, growing up in San Francisco, becoming Don Rickles’ buddy, the loss of Matthew Perry, inventing podcasts and only does one Shatner impression on this week’s “Don’t Be Alone with Jay Kogen.” Bio:Kevin Pollak is an world class actor, respected comedian, delightful impressionist…

1
Joshua Malina Shows Jay How Social Media Doesn’t Have to Ruin Your Life 1:04:33

8M ago1:04:33

1:04:33

Josh talks about acting, podcasting, being proudly Jewish without being sure about being Jewish and about not being afraid to tell his friends he loves them. Bio:Joshua Malina is an American film and stage actor (and writer) known for playing Will Bailey on the The West Wing, Jeremy Goodwin on Sports Night, US Attorney General David Rosen on Scanda…

1
Wayne Federman Decides If Jay’s Too Old To Be Funny 1:03:43

8M ago1:03:43

1:03:43

Comic, author, producer, Wayne Federman discusses if there’s an expiration date to being funny. Are you stuck in your generation or can you speak to a broader audience? That, plus what underwear to sport when shouting “Get off my lawn!” at passing children. Bio: Wayne Federman is a stand-up comic, actor, author, cultural historian, and producer. Wa…

1
Pete Holmes Explains How Jay Can Be Less Sh*tty 1:33:42

8M ago1:33:42

1:33:42

Jay is completely enthralled with the depth of comedian/writer/actor, Pete Holmes, talks about religion, philosophy, keeping your artistic standards high, staying good while being human, the joy of seeing his daughter’s face, and making his new Netflix special not so “death-y”. Bio: Pete Holmes is one of the best standup comics around. He’s the cre…

1
Aimee Mann Explains How to Survive the Music Industry 1:00:40

9M ago1:00:40

1:00:40

Singer-songwriter Aimee Mann explains creativity, writing musicals, knowing how to pick a good writing partner and how Jay should weather the crumbling TV streaming world. Just become a critically acclaimed voice of a generation. Easy peasy. Bio: Aimee Mann is a Grammy- and Oscar-nominated singer-songwriter. Mann fronted the band 'Til Tuesday with …

1
Julia Sweeney Fights Jay’s Fear of Parties 1:03:59

9M ago1:03:59

1:03:59

The funny and fabulous Julia Sweeney helps Jay fight through the fear of people, work, life, aging and the crippling danger of improv groups. Bio: Julia Sweeney started with a dream of being a Hollywood accountant and wound up becoming an actress, comedian, writer, and director known for her years on SNL and her amazing comedic one-person shows suc…

1
Steven Weber Explains Show Business 1:21:15

9M ago1:21:15

1:21:15

Actor Steven Weber helps Jay negotiate the changes in the business. Meditation, fatherhood, and convinces him that, even though they never see each other, they are true friends. Bio: Steven Weber is an actor, comedian, dad and all around delight who has acted on Broadway, TV and films but he is most at home guessing on friend’s podcasts. From Straw…

1
Introducing Don't Be Alone with Jay Kogen 1:20

9M ago1:20

1:20

Join Jay Kogen, former stand-up actor and award-winning comedy writer, as he shares his great stories from his decades in show business on his podcast, "Don't Be Alone with Jay Kogen." With a mission to fight disconnection in modern life, Jay invites funny, smart, and interesting guests to tackle life issues he's dealing with. From stand-ups to act…

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