Post Malone Invites Jimmy Olander Onstage in Cross-Generational Country Moment
August 11, 2024
In a powerful show of respect for country music’s legacy, Post Malone recently invited legendary guitarist and songwriter Jimmy Olander to join him onstage during his performance at Outside Lands in San Francisco.
Malone, who has been incorporating 1990s country favorites into his live sets, reached out to Olander after expressing admiration for Diamond Rio’s catalog — particularly the fan-favorite track “This Romeo Ain’t Got Julie Yet,” which Olander co-wrote and helped define with his signature guitar work as a member of Diamond Rio.
Rather than simply covering the song, Malone chose to honor its origin by flying Olander and his family to California and inviting him to perform it live with him onstage. The moment brought together generations of artists, blending contemporary chart power with the craftsmanship of one of Nashville’s most respected musicians.
The collaboration was widely praised by fans as a genuine gesture of musical appreciation. Malone has increasingly used his platform to spotlight the writers and players behind the hits that shaped him — and Olander’s appearance underscored the lasting influence of elite musicianship in an era that continues to rediscover the depth of 90s country.
For those who know the industry, the invitation came as no surprise. Jimmy Olander has long been regarded as a “musician’s musician” — a 2x Grammy winner, celebrated guitarist, songwriter, and arranger whose work continues to inspire artists across genres.
Jimmy Olander’s Signature Guitar Innovation Helped Redefine Modern Country Tone
9-23-25
Long before genre crossovers were common, Jimmy Olander was quietly reshaping the sound of modern country guitar from the inside out.
As the longtime lead guitarist for Diamond Rio, Olander became known not only for his precision and melodic instinct, but for pioneering a highly customized “bender” guitar system that expanded the expressive range of the instrument. Working closely with instrument builders and electronics designers, he helped refine mechanical pitch-bending techniques that allowed him to emulate pedal steel-like movement on a standard electric guitar — creating a fluid, vocal quality that became a defining part of Diamond Rio’s sound.
His technical innovation did not go unnoticed. Elite players across Nashville have cited Olander’s approach as influential, and guitar publications have documented how builders developed specialized pickups and hardware configurations to accommodate his playing style. In a genre built on tradition, Olander managed to honor the past while pushing the instrument forward.
It’s one of the reasons he is often described as a “musician’s musician” — a player whose influence extends far beyond the spotlight and into the craft itself.
Jimmy Olander’s guitar innovation didn’t happen in one single moment...(Jiimmy Olander Trivia)
12-13-25
Jimmy Olander’s guitar innovation didn’t happen in one single moment — it developed primarily during the late 1980s and early 1990s, as Diamond Rio was breaking nationally.
Diamond Rio formed in 1984, signed to Arista Nashville in 1989, and released their breakout debut single “Meet in the Middle” in 1991. It was during this early major-label period — roughly 1989–1995 — that Olander’s customized B-bender systems and signature guitar tone became widely recognized within Nashville and the broader country community.
His experimentation with multi-bender guitars (allowing multiple strings to bend independently) and collaboration with builders to refine hardware and electronics became part of Diamond Rio’s distinctive sound throughout the 1990s, particularly on their platinum-selling albums during that era.
So while the innovation evolved over years, its public impact became most visible during the band’s early-to-mid 1990s commercial peak.