Overview of Armchair Expert — Chris Stapleton
This Armchair Expert episode (hosted by Dax Shepard and Monica Padman) features country singer-songwriter Chris Stapleton in a long, wide-ranging conversation recorded in Nashville. They cover his upbringing in Kentucky, early musical path, decade-plus as a Nashville songwriter, transition to band frontman and solo star, creative habits and anxieties, family life, notable career moments (including the CMA/Justin Timberlake duet), and reflections on fame, craft, and what’s next.
Key topics covered
- Early life and family background (Staffordsville, Kentucky; father worked in coal mining and later industry)
- School years: sports, academics (valedictorian), Vanderbilt and University of Kentucky attendance
- Move to Nashville and rapid start as a staff songwriter (publishing deal within days)
- Writing career: process, co-writing culture in Nashville, hits written for other artists
- Bands and transitions: The SteelDrivers, later projects, and the shift to a solo career
- Breakthroughs and turning points: CMA duet with Justin Timberlake, TV appearances, touring
- Creative process and habits: rituals, control, tools (voice memos), relationship to deadlines
- Personal life: marriage to Morgan, family priorities, how success changed daily life
- Emotions and mental frame: perfectionism, survivor’s guilt, discomfort with fame
- Anecdotes: recording “Traveler,” the 1979 Jeep Cherokee trip, the Timberlake cabin/birthday story, a grill explosion
Who is Chris Stapleton (bio snapshot)
- Grammy-winning singer, songwriter, and guitarist known for albums including Traveller, From a Room (Vol. 1 & 2), Starting Over, and Higher (2023).
- Built his career first as a successful Nashville songwriter (many cuts and number-one singles for big country artists), then as frontman of The SteelDrivers and later a breakout solo artist.
- Married to Morgan Stapleton (both have songwriting backgrounds); they have a family and have collaborated musically.
Career highlights & timeline
- Early 2000s: Moved to Nashville to be a songwriter; got a publishing deal very quickly (described as seven days).
- Writing career: Prolific collaborator in Nashville; wrote material later recorded by mainstream country stars (examples mentioned: Kenny Chesney, Josh Turner, George Strait, Luke Bryan).
- The SteelDrivers: Bluegrass/roots band Stapleton fronted; gained critical acclaim; later left amid band tensions.
- Solo breakthrough: Solo albums (Traveller, From a Room, Starting Over, Higher) led to mainstream fame, multiple awards, and highly visible TV moments.
- High-profile collaborations/appearances: CMA performance and duet with Justin Timberlake (major turning point); contributions/appearances with artists like Taylor Swift and Adele; Super Bowl and SNL performances also noted.
Creative process and philosophy
- Songwriting approach: Often shows up to co-write with little preconception; values being present in the room and finding a role—rarely brings finished songs to sessions.
- Tools and rituals: Keeps extensive voice memos and notes; has a consistent studio chair and an old Gibson guitar he still plays—creatures-of-habit/control help his process.
- Timelines: Prefers “right” over “done”; dislikes deadlines and the pressure they create—“no such thing as a country music emergency.”
- Values: Prefers ownership/terms over immediate money when negotiating publishing/record deals; believes in long-term craft more than short-term gains.
- On output: Says he writes less now, values the “process” and is in a reflective place—unsure about how many more records he’ll make and looking for what will re-light the fire.
Personality, anxieties & life balance
- Describes himself as an extrovert who has become more reserved with fame—feels pressure to “deliver” to fans.
- Perfectionism and overthinking: Avoids mistakes, plans carefully, and can be hard on himself.
- Survivor’s guilt: Aware of talented peers who haven’t had the same luck; feels complex gratitude/guilt about success.
- Family-first considerations: Wants to balance career demands with being present for his children and wife; contemplating where to direct his focus next.
Notable anecdotes & memorable moments
- Dad and roots: Father was a coal miner/independent operator; Stapleton’s early music and record-making were partly motivated by wanting to make something his dad would like.
- Publishing deal: Met Steve Leslie and, through a quick chain of introductions, landed a publishing deal in about a week after moving to Nashville.
- “Higher”: A song he wrote in his early Nashville years that only found its place on a 2023 album—example of songs having long lives.
- SteelDrivers exit: Left (technically fired from) The SteelDrivers after a disagreement about the band’s direction.
- CMA duet with Justin Timberlake: Timberlake appearance (and the team’s eight-and-a-half minute TV slot) was pivotal; Stapleton recalled friendship, Montana birthday-cabin story, and how Justin’s professionalism helped.
- Personal rituals: Brings a specific childhood chair to the studio, maintains an old Gibson bought for $400, and has a pocket-knife roll tied to family memory.
- Grilling accident: Once had a grill gas explosion that singed hair—an example of his down-to-earth, self-deprecating storytelling.
Notable quotes (selected)
- “Silence is golden.” — On seeking silence amid family life and creativity.
- “Terms are better than money.” — On contract negotiations and valuing ownership/reversions.
- “Process is the high.” — On finding satisfaction in the work itself rather than only its outcomes.
- “There’s no such thing as a country music emergency.” — On perspective and how he handles deadlines.
Collaborations & public moments
- Appeared with Justin Timberlake (CMA performance) — credited as a major visibility boost.
- Contributed vocals/appearances with artists such as Taylor Swift and Adele (during COVID-era remote sessions).
- Performed high-profile live slots: Super Bowl, SNL, award shows and large-scale touring.
Personal & product notes
- Married to Morgan Stapleton (both have music backgrounds); family life and stability heavily influence career choices.
- Has a whiskey brand called Traveler — anecdotal mentions during the talk (they also joked about trying it).
- Collects guitars and values vintage instruments; mindful about when interests become unhealthy (discusses “lanes” of obsession versus destructive addiction).
Main takeaways
- Chris Stapleton’s success was a long, craft-centered climb: years as a staff songwriter, formative band work, and then a relatively sudden outward breakthrough that built on deep groundwork.
- His songwriting ethos is collaborative, present-focused, and ritualized—he values the room, the process, and getting things “right” more than rushing to meet deadlines.
- Fame brought comforts and constraints: professional validation and opportunities alongside discomfort, pressure to perform socially, and privacy challenges.
- Right now he’s reflective and selective—grateful, protective of family time, and searching for the next artistic fuel rather than chasing fame or output for its own sake.
Quick listening/viewing/action suggestions
- Essential music: Traveller (album), The SteelDrivers (early band records), From a Room, Starting Over, Higher.
- Notable performance to watch: CMA duet with Justin Timberlake (widely noted as a turning point).
- If interested in the backstory: search interviews or the 60 Minutes profile they reference for a deeper portrait.
If you want a super-condensed TL;DR: Stapleton is a craftsman-first songwriter who spent years writing for others, became a celebrated solo artist through steady craft plus a few catalytic live moments, and now balances family, standards, and the ongoing search for what will inspire his next creative chapter.