Uploaded April 2026 | Updated September 2026, 1 day ago
What does it take to have Steve Gadd and Will Lee playing your music before you even hit your peak years? 🎹🔥 In this episode, Rob Cass sits down with Simon Oslender, one of the most exciting rising stars in jazz, to uncover the mindset, passion, and moments that shaped his incredible journey.
Simon shares how a deep curiosity for sound started almost from childhood — from being fascinated by anything that made noise to discovering the piano as a true turning point. One of the most powerful parts of the conversation is how he earned the respect of legends like Steve Gadd and Will Lee, leading to collaborations that most musicians only dream of. We dive into his first album About Time, working with world-class rhythm sections, and why he refuses to slow down or compromise his love for playing live. His perspective is refreshing: if someone plays a wrong note — who cares? It’s all about the feeling 🎶
Beyond the achievements, Simon opens up about his musical philosophy — his love for Brazilian music, how harmony shapes his arranging, and the importance of staying authentic in a world that often pushes perfection. From touring globally to recording Grammy-nominated projects and building a sound rooted in groove and soul, his story is both inspiring and deeply human. Stick around for a special moment where Simon plays his most influential piano motifs — a glimpse into the mind of an artist who’s only just getting started ✨
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⏱️ CHAPTERS:
00:00 Rob’s Intro
00:58 How I got to play with Steve Gadd and Will Lee
07:23 I was fascinated by everything that made sound
10:53 The piano turning point
16:02 I would never cut down on gigs to do more school
18:40 I struggle to find someone who loves music as much as I do
20:56 My first album, About Time
24:28 Working with the best rhythm section in the world
31:53 When & why I use Yamaha pianos
35:32 Huge fan of Brazilian music
41:24 Dream list of artists to collaborate with
43:03 If someone plays a wrong note, who cares?
45:14 Best & worst show
51:29 How harmony influences my arranging
54:27 Steve: ‘We have to go on tour with this’
57:21 Simon Oslender plays his most influential piano motifs
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https://x.com/dopeYEAHtalk
What does it take to have Steve Gadd and Will Lee playing your music before you even hit your peak years? 🎹🔥 In this episode, Rob Cass sits down with Simon Oslender, one of the most exciting rising stars in jazz, to uncover the mindset, passion, and moments that shaped his incredible journey.
Simon shares how a deep curiosity for sound started almost from childhood — from being fascinated by anything that made noise to discovering the piano as a true turning point. One of the most powerful parts of the conversation is how he earned the respect of legends like Steve Gadd and Will Lee, leading to collaborations that most musicians only dream of. We dive into his first album About Time, working with world-class rhythm sections, and why he refuses to slow down or compromise his love for playing live. His perspective is refreshing: if someone plays a wrong note — who cares? It’s all about the feeling 🎶
Beyond the achievements, Simon opens up about his musical philosophy — his love for Brazilian music, how harmony shapes his arranging, and the importance of staying authentic in a world that often pushes perfection. From touring globally to recording Grammy-nominated projects and building a sound rooted in groove and soul, his story is both inspiring and deeply human. Stick around for a special moment where Simon plays his most influential piano motifs — a glimpse into the mind of an artist who’s only just getting started ✨
---------------------------------------------------------------------
⏱️ CHAPTERS:
00:00 Rob’s Intro
00:58 How I got to play with Steve Gadd and Will Lee
07:23 I was fascinated by everything that made sound
10:53 The piano turning point
16:02 I would never cut down on gigs to do more school
18:40 I struggle to find someone who loves music as much as I do
20:56 My first album, About Time
24:28 Working with the best rhythm section in the world
31:53 When & why I use Yamaha pianos
35:32 Huge fan of Brazilian music
41:24 Dream list of artists to collaborate with
43:03 If someone plays a wrong note, who cares?
45:14 Best & worst show
51:29 How harmony influences my arranging
54:27 Steve: ‘We have to go on tour with this’
57:21 Simon Oslender plays his most influential piano motifs
-----------------------------------------------------------------------
🎧 Don’t forget to:
👍 Like
🔔 Subscribe
💬 Comment
📲 Share
STAY TUNED ON SOCIALS:
instagram.com/dopeyeah.talk
tiktok.com/@dopeyeahtalk?_t=8pWkf42Rm9h&_r=1
facebook.com/profile.php?id=61563840578898
https://x.com/dopeYEAHtalk
