| Watching Airplanes | |
| Cover: | watching airplanes single-gary allan.jpg |
| Type: | single |
| Artist: | Gary Allan |
| Album: | Living Hard |
| Recorded: | 2007 |
| Genre: | Country |
| Length: | 4:03 |
| Label: | MCA Nashville |
| Producer: | Mark Wright, Gary Allan |
| Prev Title: | A Feelin' Like That |
| Prev Year: | 2006 |
| Next Title: | Learning How to Bend |
| Next Year: | 2008 |
"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 Allan's 2007 album Living Hard and as the twelfth of his career. The song became Allan's tenth Top 10 on the US Billboard country charts after reaching number 2 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. This song was written for and in remembrance of Allan's wife, who committed suicide and was a former flight attendant.
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 US 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.