Gallery: Outlaws! 2 of 15
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It's hard to mention Waylon Jennings without Willie Nelson. The Red Headed Stranger and his trusty guitar Trigger often collaborated with Waymore, recording such hits as "Mamma's Don't Let Your Babies Grow Up To Be Cowboys" and "Good Hearted Woman." When Willie first moved to Music City, he tried fitting in with the popular establishment which included the Nashville Sound at the time, but it wasn't a good fit for the singer-songwriter. Nelson truly found his niche after he moved back to Austin, Texas.