Alabama Gypsy Rose Jennings turned eighteen on 28 November 2025. She is the daughter of Sopranos actress Drea de Matteo and country musician Shooter Jennings, and the granddaughter of Waylon Jennings. She has no public social media accounts, has given no interviews, and has not spoken publicly about her family.
In August 2023, Drea de Matteo had ten dollars in her bank account and a house going into foreclosure. She opened an OnlyFans page at $15 a month and made $75,000 in the first seventy-five minutes. Her daughter Alabama, fifteen at the time, had told her to do it.
Alabama’s name ran in Variety, People, and Fox News throughout that period, always as context for stories about her mother rather than stories about her. She has not responded to any of it publicly.
Table of Contents
| Detail | Information |
|---|---|
| Full Name | Alabama Gypsy Rose Jennings |
| Date of Birth | 28 November 2007 |
| Age (2026) | 18 years old |
| Birthplace | New York City, USA |
| Mother | Drea de Matteo |
| Father | Shooter Jennings |
| Sibling | Waylon Albert “Blackjack” Jennings (b. 7 April 2011) |
| Paternal Grandparents | Waylon Jennings (1937-2002) and Jessi Colter |
Who Is Alabama Gypsy Rose Jennings?
Drea de Matteo and Shooter Jennings’ daughter was born on 28 November 2007 in New York City, weighing eight pounds and three ounces.
Her parents were together from 2001 to around 2013. Shooter proposed on stage at his concert in Utica, New York, in June 2009. Drea accepted in front of the crowd. They never married. Shooter wed model and actress Misty Brooke Swain in June 2013, and they have no children together.
Alabama’s younger brother is Waylon Albert “Blackjack” Jennings, born 7 April 2011, who turned fifteen in April 2026.
The Name: Where “Alabama” and “Gypsy Rose” Come From
“Alabama” comes from her father’s side. Shooter Jennings is the son of Waylon Jennings, one of outlaw country music’s central figures. The name belongs to the same Southern tradition Waylon spent his career building.
“Gypsy Rose” references Gypsy Rose Lee (1911-1970), the American burlesque performer who also worked on Broadway and in film across four decades. She became one of the most recognised performers of mid-twentieth century America and built her career on her own terms at a time when few women in that industry had that kind of control.
Neither parent has addressed publicly why they chose the name.
Her Mother: Drea de Matteo
Drea de Matteo was born Andrea Donna de Matteo on 19 January 1972 in Queens, New York. She is the youngest of three children and the only daughter. Her father Albert ran a furniture manufacturing business. Her mother Donna was a playwright who also taught at HB Studio in New York.
De Matteo trained at NYU’s Tisch School of the Arts, originally planning to direct. That changed when she auditioned for a single episode of HBO’s The Sopranos in 1999 and the producers kept expanding the role. She played Adriana La Cerva, Christopher Moltisanti’s girlfriend, across five seasons before the character was killed off in Season 5. She won the Primetime Emmy Award for Outstanding Supporting Actress in a Drama Series in 2004.
Key Roles
- The Sopranos (1999-2006) as Adriana La Cerva
- Joey (2004-2006) as Gina Tribbiani
- Desperate Housewives, Season 6 (2009-2010) as Angie Bolen
- Sons of Anarchy (2008-2014, series regular in Season 7) as Wendy Case
- Shades of Blue (2016-2018) as Detective Tess Nazario
- Nonnas (2025), alongside Vince Vaughn and Joe Manganiello
De Matteo’s career came to a near-complete stop after she refused the COVID-19 vaccine. Her agent dropped her. She launched an OnlyFans page in August 2023, telling People magazine: “OnlyFans saved my life, 100 percent. I can’t believe I’m saying that, but it really did save us.” Most of her subscribers, she said, were Sopranos fans. When asked how her children reacted, she said: “The kids were the ones who were like, ‘Do this. Show your feet. Do selfies. J. Lo and the Kardashians are always in their bikinis online, why not you?'”
In 2024, de Matteo endorsed Donald Trump for president and attended one of his campaign rallies in Coachella, California.
She now lives in Laurel Canyon, Los Angeles, according to a Variety profile from November 2024, and runs a streetwear line called Ultrafree alongside her partner, drummer Robby Staebler of UVWAYS.
Her Father: Shooter Jennings
Shooter Jennings was born Waylon Albright Jennings on 19 May 1979 in Nashville, Tennessee. He is the only child of Waylon Jennings and Jessi Colter. He grew up on his parents’ tour bus, was playing drums by age five, and moved to Los Angeles in 2001.
His debut album, Put the “O” Back in Country, came out in 2005 on Universal South Records. The lead single “4th of July” reached number 26 on the Billboard Hot Country Songs chart. Later records moved across outlaw country, Southern rock, and more experimental territory, including Countach (2016), a tribute to music producer Giorgio Moroder featuring Marilyn Manson and Brandi Carlile, and Shooter (2018), produced by Dave Cobb.
His production career has grown alongside his recording work. He co-produced Tanya Tucker’s While I’m Livin’ (2019) with Brandi Carlile, which won the Grammy for Best Country Album. By February 2023, he had three Grammys as a producer. His most recent credit is Lukas Nelson’s debut solo album American Romance, released in June 2025.
He also played a young version of his father in the Johnny Cash biopic Walk the Line (2005).
Shooter Jennings’ two children with de Matteo split their time between both parents. He has been married to Misty Brooke Swain since June 2013.
Waylon Jennings and Jessi Colter: The Inheritance
Through her father, Alabama is the granddaughter of two of the most celebrated figures in American country music.
Waylon Jennings (1937-2002) left the mainstream Nashville production circuit in the early 1970s and began producing his own records, a move that helped establish what became known as outlaw country. He was a founding member of The Highwaymen alongside Johnny Cash, Willie Nelson, and Kris Kristofferson. He died on 13 February 2002 of diabetic complications in Chandler, Arizona, five years before Alabama was born. A posthumous album, Songbird, charted in October 2025.
Her grandmother is Jessi Colter, born Mirriam Johnson on 25 May 1943 in Phoenix, Arizona. She took her stage name from a relative who rode with Jesse James. Her 1975 single “I’m Not Lisa” reached number one on the country charts and crossed into the pop top five. Wanted! The Outlaws (1976), which she recorded with Waylon Jennings, Willie Nelson, and Tompall Glaser, became the first country album in history to sell one million copies. Jessi Colter is 82 years old.
As a Waylon Jennings granddaughter, Alabama carries a musical heritage that most people in the industry spend their entire careers chasing.
What We Know About Alabama in 2026
At eighteen, Alabama is the older of Shooter Jennings and Drea de Matteo’s two children and one of the more private celebrity daughters in American entertainment, given who her parents are. She has no confirmed social media accounts and has given no interviews at any point in her life.
The clearest on-record picture of her home life came in July 2024, when de Matteo appeared on the podcast Not Today, Pal with Sopranos co-stars Robert Iler and Jamie-Lynn Sigler. Before de Matteo had started speaking, Iler passed along a message: her son Waylon, then thirteen, had been standing outside the recording room asking which part of his mother’s OnlyFans photos needed airbrushing. De Matteo laughed, then caught herself. “My kids are out there. I’m sorry, guys. I’m really sorry. But they know.”
In a Fox News Digital interview around the same time, de Matteo confirmed that Alabama had also been helping edit photos for the page and that both children had backed the decision from the start.
Alabama has said nothing about any of it. Nothing about her public profile has changed since she turned eighteen.
She was named after a performer who spent her career refusing to be told what to do. Her mother, in 2023, did much the same thing. Whether Alabama follows any version of that path, nobody outside her family can say yet. Whatever comes next is hers to work out.
