Watch the video at the end of this article.
Introduction
Alan Jackson’s “Tall, Tall Trees” – From Hidden Gem to Chart-Topping Hit
Released in October 1995 as part of The Greatest Hits Collection, Alan Jackson’s “Tall, Tall Trees” quickly soared to the top of the Billboard Hot Country Singles chart, becoming his eleventh Number One hit. Yet the song’s journey began nearly four decades earlier, rooted in the golden age of country music.
The track was originally recorded in 1957 by George Jones as the B-side to “Hearts in My Dream.” Co-written by Jones and the incomparable Roger Miller, the song combined Miller’s signature humor with Jones’s gift for traditional country storytelling. Its lighthearted charm made it a standout, even if it remained in the shadows of Jones’s more famous work at the time.
Roger Miller revisited the tune in 1970, recording his own version for A Trip in the Country. Still, the song waited patiently for its true breakthrough until Jackson—already celebrated for his neotraditional style—rediscovered it while combing through catalogs for material to include on his compilation. Struck by its Cajun-inspired bounce and playful lyrics, he recorded it almost on a whim. As he later admitted in the liner notes, Jackson “stumbled across” the song, only realizing afterward that both Jones and Miller were behind it.
Jackson’s version preserves the lighthearted spirit of the original promise—“I’ll buy you tall, tall trees and all the waters in the seas”—but enriches it with a lively arrangement of accordion, fiddle, steel guitar, and his signature vocal twang. Critics praised the track for blending heartfelt devotion with fun, making it feel both fresh and timeless. Country historian Kevin John Coyne even described it as the crown jewel of Jackson’s mid-’90s run, noting how he breathed new life into the song in a way that surpassed earlier renditions.
The playful music video, directed by Sherman Halsey, mirrored the song’s whimsical charm with quirky imagery: a barefoot woman in a stark white room, a smitten suitor, and even a peanut butter sandwich.
By reviving “Tall, Tall Trees,” Jackson not only honored two country legends but also cemented the song’s place in country music history—transforming it into a joyful anthem of love and generosity.