- Portrayed his father, country music legend Waylon Jennings, in the film Walk the Line (2005).
- Son of Waylon Jennings & Jessi Colter.
- Father of his 2nd child with ex-girlfriend and now ex-fiancé Drea de Matteo, son Waylon Albert "Blackjack" Jennings, born on April 7, 2011.
- Is the only child of his mother & father, however, both Waylon & Jessi have children from previous marriages.
- Father of his 1st child with ex-girlfriend and now ex-fiancé Drea de Matteo, daughter Alabama Gypsy Rose Jennings, born 28 November 2007, weighing 8lbs., 3oz. Mother is Drea de Matteo.
- Seven years younger than his ex-girlfriend, Drea de Matteo.
- Was engaged to Drea de Matteo [June 2009-2013].
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