Songfacts®:

• This broken-hearted lament finds Willie Nelson at the mercy of a whiskey habit. He begs the river of booze to never run dry because it's the only thing that numbs the pain of a breakup. The song debuted a year earlier on the album Whiskey River by Johnny Bush, a Texas-born country singer who wrote the tune with composer Paul Stroud, and peaked at #14 on the country chart.
  
  Although Nelson is a celebrated songwriter, the cover helped establish his prowess as an interpreter and became one of his signature hits. He's since opened nearly all of his concerts with the song.
• Nelson and Bush were longtime friends by the time Nelson covered this. Back when he was working as a DJ at a Texas radio station, Nelson was also playing gigs in Bush's band. They performed together in Ray Price's band, The Cherokee Cowboys, in the early '60s, and again when Bush played in a couple of Nelson's groups, the Offenders and the Record Men. "And then Johnny wrote 'Whiskey River,'" Nelson wrote in the foreword to Bush's book Whiskey River (Take My Mind): The True Story of Texas Honky-Tonk. "He has been exceedingly wealthy ever since. He doesn't need to sing any more or write books. He only does it to serve his public, which he deeply loves."
• Nelson's version wasn't released as a single until 1978, when it was featured on his live album Willie and Family Live. It peaked at #12 on the country chart. The single also earned Nelson a Grammy nomination for Best Country Vocal Performance, Male (Kenny Rogers won for "The Gambler").
• Around the time the original version was released, Bush inexplicably lost his voice. He had been struggling to hit high notes for a while, but didn't realize it was anything serious. It took years to finally find a correct diagnosis, which was spasmodic dysphonia, a neurological condition that strikes one out of 35,000 people. Vocal exercises helped him regain most of his singing ability, but his producer Tommy Hill insisted if it wasn't for the affliction, Bush would've become one of the biggest voices in the industry.
• Nelson also sang this with The Highwaymen, a country supergroup that included Johnny Cash, Kris Kristofferson and Waylon Jennings. Jennings and his wife Jessi Colter also provided backing vocals and instrumentation on the Shotgun Willie album. The Highwaymen's version was used on the video game Grand Theft Auto V.
• Nelson performed this on Saturday Night Live in 1977.
• Toby Keith, who collaborated with Nelson on the 2002 duet "Beer For My Horses," referenced this song on the Shock'n Y'all bonus track "Weed with Willie" the following year: "You can pour me some old whiskey river my friend, but I'll never smoke weed with Willie again."
• Nelson sang this as a duet with Sheryl Crow on the 2002 live album Willie Nelson & Friends – Stars & Guitars.
• The song inspired the dance hall/bar & grill Whiskey River in Houston, Texas.
• Nelson helped market a Kentucky bourbon brand called Old Whiskey River.
• This was featured on the sitcom My Name Is Earl in the 2006 episode "Van Hickey."