"Watching Airplanes" is a song written by Jim Beavers and Jonathan Singleton, and recorded by American country music singer Gary Allan. It was released in July 2007 as the first single from his album Living Hard. As his twentieth chart single overall, the song reached a peak of number 2 on the Billboard country charts in early 2008. "Watching Airplanes" was nominated for the 'Single Record of the Year' at the 43rd Annual Academy of Country Music Awards on May 18, 2008.

The song was also included on the compilation album, Now That's What I Call Country.

The music video for this song was shot during live concerts at Red Rocks Amphitheatre in Morrison, Colorado, the Red Dirt Roundup '07 in Fort Worth, Texas, the Nutty Brown Cafe in Austin, Texas, and in Saint George, Utah.

"Watching Airplanes" debuted at number 53 on the U.S. Billboard Hot Country Songs chart for the week of August 4, 2007. After spending 31 weeks on the chart, it peaked at number 2 for the chart week of March 1, 2008.

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