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.