Watch the video at the end of this article.
Introduction
Released in October 1995 as part of Alan Jackson’s The Greatest Hits Collection, “Tall, Tall Trees” became his eleventh Number One hit on the Billboard Hot Country Singles chart . But the tune’s story goes much deeper, tracing its roots back to 1957, when the legendary George Jones first recorded it as the B‑side to “Hearts in My Dream” . Co‑written by Jones and the inimitable Roger Miller, the song showcases Miller’s trademark wit and Jones’s traditional country storytelling .
Roger Miller later included his own version on his 1970 album A Trip in the Country, further establishing the song’s place in the country canon . Yet it took nearly four decades for the song to truly reach its peak—when Jackson, already celebrated for his authentic neotraditional style, decided to revive the track. He encountered it while digging through the catalogs, was charmed by its buoyant Cajun-tinged rhythm, and couldn’t resist recording it among two new songs featured on his hits compilation . As Jackson revealed in the liner notes, he “stumbled across” the song, and only after recording it did he learn of Jones’s—and Miller’s—authors’hip .
Jackson’s rendition maintains the song’s playful promise—“I’ll buy you tall, tall trees and all the waters in the seas”—but elevates it with a spirited arrangement featuring accordion, fiddle, steel guitar, and that unmistakable twang . Critics praised his performance for perfectly balancing devotion and fun, resulting in a fresh yet timeless revival. Indeed, music historian Kevin John Coyne called it the highlight of Jackson’s golden era, noting how he outshines even the original renditions .
The accompanying music video, directed by Sherman Halsey, features whimsical scenes—a barefoot woman in a white room, a charming suitor, and a peanut-butter sandwich—visually echoing the song’s playful spirit. By breathing new life into a hidden classic, Jackson not only paid homage to two country legends but also solidified the song’s place as a joyful declaration of love and largesse.