Waylon Jennings — Drinkin’ and Dreamin’

A Song Born Between Recovery, Restlessness, and the Open Road

The Era Behind the Song

By 1985, Waylon Jennings was already a legend. The pioneer of outlaw country had spent more than a decade reshaping the genre with raw honesty, grit, and a refusal to conform. But the mid-1980s brought a turning point. The recording sessions for his album Turn the Page, including Drinkin’ and Dreamin’, took place after Jennings completed treatment for long-term cocaine addiction.

In his memoir and interviews from that period, Waylon spoke openly about reclaiming clarity — physically, mentally, and creatively. He described the sessions as the first time in years that he was recording in a cleaner state, a stark contrast to the haze that surrounded parts of his 1970s and early 1980s work. That context gave the album emotional weight. It wasn’t just music anymore — it was proof of survival, even if the themes still carried his signature longing for escape.

Release and Production

Drinkin’ and Dreamin’ was written by Troy Seals and Max D. Barnes, two highly respected Nashville songwriters. Jennings recorded the track under RCA Records, and it was released as a 7-inch single in June 1985 as the lead single from Turn the Page.

The song featured “Prophets Show Up in Strange Places” on the B-side, another Jennings recording from the same album cycle. The production of the track was handled by Jerry Bridges and Gary Scruggs, who also produced the rest of the album. With a runtime of approximately three minutes, the song was crafted for country radio — punchy, tight, and melodic, but thematically heavy.

Chart Success

Despite the turbulence Jennings had recently left behind, the song proved that his commercial appeal remained intact. In the United States, Drinkin’ and Dreamin’ climbed the Billboard Hot Country Singles & Tracks chart, peaking at No. 2 in 1985 — one of his strongest chart performances of the decade.

In Canada, the song reached the mid-20s on RPM’s Country Tracks survey, confirming moderate but documented airplay. While it didn’t dominate Canadian charts the way it did in the U.S., its presence still contributed to Jennings’s steady 1980s visibility in North American country music.

Presence in His Discography

Though not positioned at the start of the album, the song appeared in the latter half of Turn the Page’s LP tracklist, where it served as one of the key promotional songs used to push the album to radio.

Later compilations of Jennings’s work frequently included Drinkin’ and Dreamin’, cementing it as one of his defining 1980s hits. Discography listings also document the original 7-inch release under an RCA catalog number in the 14000 series, crediting Seals and Barnes as writers and linking it directly to Turn the Page.

Themes and Meaning

At its heart, Drinkin’ and Dreamin’ is a song about contradiction — the desire to run, paired with the certainty of staying. The narrator works a job he hates and feels misunderstood at home. He imagines driving toward Texas, L.A., or Old Mexico, but admits:

“Drinkin’ and dreamin’, knowing damn well I can’t go.”

It’s escapism without departure. The bar table becomes the only place where he can mentally roam free, leaving behind the suffocating disguise of a suit and tie. The lyrics echo Jennings’s lifelong motifs — freedom, confinement, the wind, the road — but now tinged with a different subtext.

After addiction recovery, the song takes on an unintended double meaning: Waylon himself had just escaped something destructive, yet the song insists that some escapes are emotional, not geographical.

The Music and the Myth

Waylon Jennings built his career on songs that sounded like truth even when sung through metaphor. Drinkin’ and Dreamin’ fits that tradition perfectly. It carries the rough voice of a man who has lived hard, but the cleaner chapter he had entered gave the song sharper edges — more reflective, more human, more resigned than rebellious.

Even without flashy storytelling or dramatic instrumentation, the song works because of Waylon’s delivery. He didn’t sing about leaving the road — he sang like someone who had already been on it too long to pretend the dream wasn’t real.

Legacy

Drinkin’ and Dreamin’ remains one of the most memorable singles from Waylon’s 1980s catalog, not because it changed country music, but because it revealed something timeless:

Some people aren’t trapped by distance.
They’re trapped by circumstance, longing, and identity — and sometimes dreaming is the only form of leaving they have left.

And in 1985, Waylon Jennings, newly sober and still restless, was the perfect man to sing it.