In 2003, just as his first single When You Come Around was released, he celebrated his first No. 1 as a songwriter when friend and collaborator Dierks Bentley took the Ruttan/Bentley/Brett Beavers co-write "What Was I Thinkin'" to the top of the charts in the US.
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Outside of writing for his own albums, Ruttan has co-written songs for many artist including; "What Was I Thinkin'" and "Lot of Leavin' Left to Do" by Dierks Bentley, "Hold My Beer" and "My Way" by Aaron Pritchett, "Guys Like Me" and "Hell on the Heart" by Eric Church, "Promise Broken" by Gary Allan, "Shotgun Girl" by The JaneDear Girls, and many more.
The video features Lauren Elaine as 'Becky', the white tank-top wearing "beauty from South Alabama".
The music video was the third directed by Peter Zavadil, and the video costars Lauren Elaine reprising her role as "Becky" from "What Was I Thinkin'".