Uploaded December 2025 | Updated September 2026, 3 weeks ago
Ray Romano sits down for a wide-ranging conversation about the moments that shaped his life and career — from getting held up at gunpoint as a teenager working at a Queens gas station, to the early stand-up grind in New York, to the TV appearances that changed everything. Episode debuted nationwide in 2016.
#interview #podcast #comedy
00:00 Intro + Ray’s early hustle in Queens
00:24 Held up at gunpoint (twice) working at a gas station
03:54 First stand-up set + the “Jackie Roberts” alias
06:00 The NYC comedy grind (multiple shows a night, parking tickets)
07:36 Johnny Carson: pre-set panic + the sprint back for notes
10:03 Why Letterman changed everything
12:19 The “don’t cut your pants” moment before his first Letterman set
15:18 Ray’s relationship with Letterman + final appearance emotions
17:17 Everybody Loves Raymond: terrible first-season ratings + “do or die” move to Mondays
19:51 When Ray knew the show had real chemistry (“Standard Deviation”)
22:28 Ending Raymond on top (why they stopped at season 9)
25:49 Life after the show: identity, therapy, and finding the next thing
28:43 Growing up in Queens: awkward 7th grade dance story
32:05 Flunking out, switching schools, and being a “slack off”
33:18 Early performing bug: church plays, SNL influence, “No Talent Incorporated”
35:14 Acting class monologue about his father (and getting emotional)
39:08 How his upbringing shaped him (affection, parenting, insecurity)
40:07 Meeting his wife at the bank + dating stories
42:23 Success insecurity + Emmy psychology
44:32 What he misses about being an unknown comic
45:47 Bombing early on + quitting stand-up (twice)
47:21 Handling criticism + reading comments online
50:20 Turning real life into stand-up (son runs out of gas on the 101)
52:25 Building bits + writer friends helping with tags
54:55 How long it takes to perfect a bit
56:19 Sports childhood + coaching + “go outside” era
58:08 Golf obsession + CBS perks (Lakeside membership)
58:58 Augusta after The Masters (Press Day) + trying to break 100
01:00:53 Pebble Beach stories + “prime time” tee times
01:03:13 Tiger Woods pace-of-play controversy + Sports Illustrated article
01:05:38 Hank Haney Project: best lesson + “don’t think about your score”
01:07:34 Mind-bets, gambling discipline, and the TV-in-a-chair loophole
Become a member to watch full episodes and get exclusive access to content: bit.ly/3q4TjAb
Subscribe to watch the latest interviews: bit.ly/1R1Fd6w
Ray Romano sits down for a wide-ranging conversation about the moments that shaped his life and career — from getting held up at gunpoint as a teenager working at a Queens gas station, to the early stand-up grind in New York, to the TV appearances that changed everything. Episode debuted nationwide in 2016.
#interview #podcast #comedy
00:00 Intro + Ray’s early hustle in Queens
00:24 Held up at gunpoint (twice) working at a gas station
03:54 First stand-up set + the “Jackie Roberts” alias
06:00 The NYC comedy grind (multiple shows a night, parking tickets)
07:36 Johnny Carson: pre-set panic + the sprint back for notes
10:03 Why Letterman changed everything
12:19 The “don’t cut your pants” moment before his first Letterman set
15:18 Ray’s relationship with Letterman + final appearance emotions
17:17 Everybody Loves Raymond: terrible first-season ratings + “do or die” move to Mondays
19:51 When Ray knew the show had real chemistry (“Standard Deviation”)
22:28 Ending Raymond on top (why they stopped at season 9)
25:49 Life after the show: identity, therapy, and finding the next thing
28:43 Growing up in Queens: awkward 7th grade dance story
32:05 Flunking out, switching schools, and being a “slack off”
33:18 Early performing bug: church plays, SNL influence, “No Talent Incorporated”
35:14 Acting class monologue about his father (and getting emotional)
39:08 How his upbringing shaped him (affection, parenting, insecurity)
40:07 Meeting his wife at the bank + dating stories
42:23 Success insecurity + Emmy psychology
44:32 What he misses about being an unknown comic
45:47 Bombing early on + quitting stand-up (twice)
47:21 Handling criticism + reading comments online
50:20 Turning real life into stand-up (son runs out of gas on the 101)
52:25 Building bits + writer friends helping with tags
54:55 How long it takes to perfect a bit
56:19 Sports childhood + coaching + “go outside” era
58:08 Golf obsession + CBS perks (Lakeside membership)
58:58 Augusta after The Masters (Press Day) + trying to break 100
01:00:53 Pebble Beach stories + “prime time” tee times
01:03:13 Tiger Woods pace-of-play controversy + Sports Illustrated article
01:05:38 Hank Haney Project: best lesson + “don’t think about your score”
01:07:34 Mind-bets, gambling discipline, and the TV-in-a-chair loophole
Become a member to watch full episodes and get exclusive access to content: bit.ly/3q4TjAb
Subscribe to watch the latest interviews: bit.ly/1R1Fd6w
![Stephen A. Smith [Preview]](https://i.ytimg.com/vi/koUnhh8BWlU/mqdefault.jpg "Stephen A. Smith [Preview]
More than 20 years after first interviewing him on a high school radio show, Graham Bensinger reunites with ESPN star Stephen A. Smith — this time with rare, behind-the-scenes access. Graham follows Stephen A. from the First Take studio in New York to the headquarters of Straight Shooter Media, and inside his private Miami home — a space he rarely opens to anyone. During their time together, Smith reflects on family loss, his ESPN firing and comeback, and his growing political aspirations — including why he says he’d only consider the presidency.
#tvshow #espn #stephenasmith
Become a member to watch full episodes and get exclusive access to content: https://bit.ly/3q4TjAb
Subscribe to watch the latest interviews: http://bit.ly/1R1Fd6w
Episode debuted nationwide in 2026.")
