John AlexAlabama Gypsy Rose Jennings is an American celebrity child who has been in the public eye since birth, thanks to her parents’ immense fame. Born on November 28, 2007, she is the daughter of Drea de Matteo, the Emmy-winning actress best known for her roles in The Sopranos and Desperate Housewives, and Shooter Jennings, an acclaimed country-rock musician and the son of music legends Waylon Jennings and Jessi Colter.
Being born into such a prominent artistic family has naturally placed Alabama in the spotlight, though her parents have tried to provide her with a grounded, creative upbringing. With her heritage rooted deeply in Hollywood and country music royalty, Alabama represents the continuation of two American entertainment dynasties.
| Details | Information |
|---|---|
| Full Name | Alabama Gypsy Rose Jennings |
| Date of Birth | November 28, 2007 |
| Age (as of 2025) | 17 Years |
| Birthplace | Los Angeles, California, USA |
| Nationality | American |
| Ethnicity | Italian-American and Southern U.S. Heritage |
| Parents | Father: Shooter Jennings (Musician) Mother: Drea de Matteo (Actress) |
| Grandparents (Paternal) | Waylon Jennings (Country Music Legend), Jessi Colter (Singer-Songwriter) |
| Grandparents (Maternal) | Albert de Matteo, Donna de Matteo |
| Siblings | Waylon Albert “Blackjack” Jennings (Brother) |
| Profession | Celebrity Child, Aspiring Creative Artist |
| Known For | Being the daughter of Drea de Matteo and Shooter Jennings |
| Education | Attending school in Los Angeles (Private) |
| Religion | Christianity |
| Residence | Los Angeles, California, USA |
| Languages | English |
| Zodiac Sign | Sagittarius |
| Net Worth | N/A (Minor) |
| Family Net Worth | Approx. $22 million combined (Parents) |
| Interests | Music, Acting, Art, Family Life |
| Famous Relatives | Margot Robbie (Family Friend – Industry Connection), Waylon Jennings (Grandfather) |
| Public Image | Grounded, Creative, and Kind-Hearted Teen |
| Future Aspirations | Likely to pursue acting or music, inspired by her family’s legacy |
Early Life and Family Background
Born in Los Angeles, California, Alabama Gypsy Rose Jennings grew up surrounded by artistry, fame, and creativity. Her family background is a fascinating blend of Hollywood drama and Nashville soul — a combination that reflects her parents’ unique paths.
Her mother, Drea de Matteo, achieved fame for playing Adriana La Cerva in HBO’s The Sopranos, a role that earned her an Emmy Award and critical acclaim. Her father, Shooter Jennings, is the only son of Waylon Jennings, a pioneer of the outlaw country movement, and Jessi Colter, one of the most respected female artists in country music history.
This lineage makes Alabama Jennings a fourth-generation creative — destined to carry forward the spirit of music, acting, and artistry in her own unique way.
Meaning Behind the Name “Alabama Gypsy Rose Jennings”
The name “Alabama Gypsy Rose Jennings” holds deep personal and cultural significance. Her first name, Alabama, pays homage to the Southern roots of her father’s family and the legacy of Waylon Jennings, who often drew inspiration from his Southern upbringing.
The middle name, Gypsy Rose, reflects the family’s artistic spirit and possibly hints at the free-spirited, creative lifestyle embraced by both her parents. Together, the name symbolizes heritage, individuality, and freedom — three traits that define the Jennings family legacy.
Family Tree: A Legacy of Music and Acting
The Jennings–de Matteo family tree is filled with influential figures from American entertainment history.
- Father: Shooter Jennings – singer-songwriter, record producer, and radio personality known for blending rock and country genres.
- Mother: Drea de Matteo – actress recognized for her roles in The Sopranos, Sons of Anarchy, and Desperate Housewives.
- Grandparents: Waylon Jennings and Jessi Colter on her father’s side, both music icons.
- Maternal grandparents: Albert de Matteo and Donna de Matteo.
- Great-grandparents: William Alvin Jennings and Lorene Beatrice Shipley.
This rich artistic lineage has created an environment filled with creativity, inspiration, and respect for the arts — one that Alabama Jennings has grown up immersed in.
Relationship with Her Parents
Although her parents, Drea de Matteo and Shooter Jennings, separated years ago, they continue to co-parent Alabama and her older brother, Waylon Albert Jennings, with love and cooperation.
Drea has often spoken publicly about how much her children mean to her, sharing moments of their lives on social media. Shooter, too, has expressed deep affection for his kids, balancing his busy touring schedule with fatherhood.
Both parents emphasize normalcy, creativity, and authenticity in their children’s upbringing — teaching them the value of hard work and humility despite their celebrity heritage.
Growing Up in the Spotlight
From a young age, Alabama Gypsy Rose Jennings has attracted public curiosity. With her parents frequently appearing in media interviews and red-carpet events, she has occasionally made public appearances alongside them.
Despite this, her parents have made a conscious effort to shield her from excessive media attention, focusing instead on providing a well-rounded childhood filled with art, education, and love.
In recent years, as she has grown into her teenage years, Alabama has started to build her own online presence, occasionally appearing in photos or videos with her mother on social media platforms.
Siblings and Family Bond
Alabama Jennings has one older brother, Waylon Albert “Blackjack” Jennings, born in April 2011. Named after their legendary grandfather, Waylon, her brother also shows interest in music and technology.
The Jennings siblings share a close relationship, often seen together in family photos shared by their parents. Their family dynamic blends modern parenting with the deep-rooted traditions of Southern and Italian-American culture.
Mother: Drea de Matteo’s Influence
Drea de Matteo, Alabama’s mother, is one of the most respected actresses in television history. Her portrayal of Adriana in The Sopranos remains one of TV’s most memorable performances, earning her a Primetime Emmy Award in 2004.
Beyond acting, Drea is known for her down-to-earth personality and resilience. She’s been candid about motherhood, financial struggles, and rebuilding after personal challenges, including losing her home in a fire in 2015.
For Alabama, having such a strong, independent mother has been a guiding influence — teaching her empathy, perseverance, and self-confidence.
Father: Shooter Jennings’ Musical Legacy
Shooter Jennings, Alabama’s father, is a Grammy-winning musician who has carried forward the outlaw country legacy of his father, Waylon Jennings.
Born and raised in Nashville, Shooter began playing instruments as a child and later forged his own musical path, blending rock, electronic, and country sounds. He has released multiple acclaimed albums and produced records for other notable artists.
Shooter’s approach to music — fearless and genre-defying — likely inspires Alabama’s creative curiosity and love for art.
Grandparents: Waylon Jennings and Jessi Colter
On her father’s side, Alabama Jennings belongs to one of the most storied families in American country music.
Her grandfather, Waylon Jennings (1937–2002), was a trailblazer who helped define the outlaw country movement in the 1970s, along with Willie Nelson and Johnny Cash. He was inducted into the Country Music Hall of Fame in 2001.
Her grandmother, Jessi Colter, is a celebrated singer-songwriter best known for her hit “I’m Not Lisa.” Together, they redefined the sound of country music with authenticity and grit.
Having grown up hearing stories about them, Alabama carries their musical spirit and cultural legacy forward.
Maternal Heritage: The De Matteo Side
On her mother’s side, Alabama Jennings inherits Italian-American roots from Drea de Matteo’s family, who hail from New York City. Her maternal grandparents, Albert and Donna de Matteo, provided a strong sense of tradition and culture that Drea has passed down to her children.
This Italian-American influence complements the Southern musical roots from her father’s side, giving Alabama a rich cultural identity that blends two distinct but passionate heritages.
Education and Interests
While her educational details remain private for safety reasons, it is known that Alabama Jennings attends school in Los Angeles, where she balances academics with creative activities.
Like her parents, she has a growing interest in music, acting, and art. According to family interviews, Alabama enjoys playing musical instruments and exploring creative projects — though her parents have emphasized that she’s free to choose her own path, whether inside or outside of show business.
Personality and Public Image
Those who have met Alabama Gypsy Rose Jennings often describe her as intelligent, kind-hearted, and mature for her age. Despite being born into fame, she is known for her humble and grounded nature — a testament to her parents’ efforts to raise her outside the chaos of Hollywood.
She maintains a relatively low public profile, occasionally seen in family posts or attending public events with her mother. Fans admire her for her natural charm and resemblance to both her parents.
Presence on Social Media
While Alabama Jennings does not have official public social media accounts, she sometimes appears in photos and videos shared by Drea de Matteo on Instagram.
Drea often shares glimpses of family life, showing Alabama’s humor, creativity, and love for animals. Her occasional online presence gives fans a rare but genuine look into her family’s bond and lifestyle.
Life Away from Hollywood Glare
Unlike many celebrity children who are thrust into the spotlight, Alabama Jennings has enjoyed a relatively private upbringing. Her parents have worked hard to provide her with normalcy — allowing her to explore life at her own pace.
They value privacy and have avoided overexposing their children to the media, ensuring Alabama can grow up with the freedom to discover her passions organically.
Future Aspirations
As of now, Alabama Gypsy Rose Jennings has not publicly expressed her career goals, but given her lineage, it wouldn’t be surprising if she eventually pursued a path in acting, music, or creative arts.
With the guidance of her talented parents and the inspiration of her grandparents’ legendary achievements, Alabama has the potential to make a mark in whichever field she chooses.
Net Worth and Family Wealth
At 17 years old, Alabama Jennings does not have an independent net worth. However, she belongs to a financially established family. Her mother, Drea de Matteo, has an estimated net worth of $10 million, while her father, Shooter Jennings, is estimated to be worth around $12 million.
The Jennings-de Matteo family enjoys a comfortable lifestyle supported by their successful entertainment careers.
Conclusion: Carrying Two Great Legacies Forward
Alabama Gypsy Rose Jennings stands at the intersection of two powerful entertainment worlds — Hollywood and country music. With a mother celebrated for her acting brilliance and a father rooted in musical innovation, she embodies the best of both her family’s heritages.
Though still young, Alabama’s life already reflects the values of creativity, independence, and authenticity. As she steps into adulthood, the world eagerly awaits to see whether she will continue her family’s artistic legacy or create her own unique path.
Whatever her future holds, one thing is certain: Alabama Jennings represents a new generation of talent, grace, and inspiration.
Frequently Asked Questions (FAQs)
1. Who is Alabama Gypsy Rose Jennings?
Alabama Jennings is the daughter of actress Drea de Matteo and musician Shooter Jennings, born on November 28, 2007.
2. How old is Alabama Gypsy Rose Jennings?
She is 17 years old, as of 2025.
3. Who are Alabama Jennings’ grandparents?
Her grandparents are Waylon Jennings, Jessi Colter, Albert de Matteo, and Donna de Matteo.
4. Does Alabama Jennings have siblings?
Yes, she has one older brother, Waylon Albert “Blackjack” Jennings.
5. What is Alabama Jennings known for?
She is known as the daughter of two famous entertainers and for being part of both Hollywood and country music’s royal families.
6. Are Alabama Jennings’ parents still together?
No, Drea de Matteo and Shooter Jennings separated, but they maintain a friendly co-parenting relationship.
7. What is Alabama Jennings’ nationality?
She is American, with Italian-American and Southern U.S. heritage.
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