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Jennings was previously in a relationship with actress Drea de Matteo. They met in 2003. Shooter Jennings Kids. Jennings is a proud father to two kids, a daughter Alabama Gypsyrose Jennings born on November 28, 2007, and son Waylon Albert “Blackjack” Jennings born on April 2011 from his first marriage with actress Drea de Matteo.
Jennings began dating actress Drea de Matteo in 2001. They have two children together, a daughter born in 2007 and a son born in 2011. Jennings and de Matteo eventually ended their relationship without marrying. Jennings married long-time friend Misty Brooke Swain on June 4, 2013, in Joshua Tree, California.
Apr 7, 2011 · Shooter Jennings, son of country music Outlaw legend Waylon Jennings and Jessi Colter, along with his long-time partner and fiance, Drea De Matteo, most famous as “Adriana” from The Sopranos, have given birth to a baby boy with a famous first name: “Waylon Albert “Blackjack” Jennings”.
De Matteo started dating musician Shooter Jennings in 2001. They became engaged on June 11, 2009, when Jennings proposed onstage at the Stanley Theater during a show in Utica, New York. They have two children together. Jennings and de Matteo eventually ended their relationship without marrying.
- Shooter Jennings. Born Waylon Albright, Shooter is the only son to come from Jennings's marriage to fourth wife, Jessi Colter. He was born shortly after his parents moved to Nashville.
- Terry Vance Jennings. Terry Jennings was Jennings's oldest child from his first marriage to Maxine Caroll Lawrence. He traveled on tour with his father, initially just selling merchandise before eventually becoming his production manager.
- Buddy Dean Jennings. Buddy Dean was another child that came from Jennings and Maxine Lawrence's marriage. When Jennings was first getting his start in the music world, he was a skilled guitarist who landed himself a gig as a bass player in Buddy Holly's band.
- Julie Rae Jennings. Julie Rae was Buddy and Terry's sister from Jennings and Maxine's marriage. Sadly, she passed away in 2014 after losing a battle to cancer.
Apr 8, 2011 · The couple's first child, daughter Alabama Gypsyrose, is 3. The son of Waylon Jennings and Jessi Colter, Shooter's given name is Waylon Albright Jennings. He and de Matteo have been...
Apr 8, 2011 · Congratulations to Shooter Jennings and fiancée, actress Drea de Matteo, who have announced the arrival of their second child, a son who will carry on the family name. Shooter broke...
