5 Shocking Revelations About Drea De Matteo's Love Life And Her OnlyFans Financial Lifeline

Drea de Matteo's private life has always been as dramatic and compelling as her most famous on-screen roles, but in the last few years, the Emmy-winning actress has made headlines for reasons far beyond Hollywood. As of December 2025, the star, best known as Adriana La Cerva on *The Sopranos*, has navigated a tumultuous journey involving rockstar partners, two children, a broken engagement, and a highly publicized pivot to the adult content platform OnlyFans, which she claims saved her from financial ruin. Her current relationship status remains a subject of intense curiosity, with reports linking her to a new musician, while she continues to leverage her newfound career to express controversial political views. The current buzz centers on her rumored relationship with musician Robby Staebler, a drummer from the band UVWAYS, though official confirmation is often elusive in the celebrity world. This new chapter follows her long-term, high-profile relationships with country music's Shooter Jennings and Whitesnake bassist Michael Devin, creating a fascinating timeline of a woman who consistently chooses partners from the world of rock and roll. This deep dive explores the full, complex story of Drea de Matteo’s romantic entanglements and the controversial career moves that have defined her life after the prestige television era.

Drea de Matteo: Full Biography and Career Milestones

Andrea Donna de Matteo, known professionally as Drea de Matteo, is an American actress whose career spans over three decades, marked by iconic roles in critically acclaimed television series. Her journey from a New York native to an Emmy Award winner is a testament to her raw talent and powerful on-screen presence.

• Full Name: Andrea Donna de Matteo
• Date of Birth: January 19, 1972
• Place of Birth: Queens, New York, U.S.
• Ancestry: Italian-American
• Education: Graduated from the Tisch School of the Arts at New York University.
• Breakout Role: Adriana La Cerva on the HBO series *The Sopranos* (1999–2006).
• Major Accolade: Won the Primetime Emmy Award for Outstanding Supporting Actress in a Drama Series in 2004 for her role in *The Sopranos*.
• Other Notable Roles: Gina Tribbiani, Joey Tribbiani's sister, on the NBC sitcom *Joey* (2004–2006); Wendy Case on the FX series *Sons of Anarchy* (2008–2014); and Angie Bolen on *Desperate Housewives* (2009–2010).
• Children: Two children with Shooter Jennings: daughter Alabama Gypsyrose Jennings (born 2007) and son Waylon Albert "Blackjack" Jennings (born 2011).
• Entrepreneurial Venture: Co-owned a vintage clothing store in the East Village, New York, called Filth Mart with former boyfriend Michael Sportes from 1997 to 2004.

From Mob Wives to Musicians: Drea de Matteo's High-Profile Relationship Timeline

Drea de Matteo's romantic life has a consistent theme: a strong attraction to musicians and artists. Her relationship history is a clear list of long-term commitments, including a decade-long partnership and a public engagement.

Michael Sportes: The Early Entrepreneurial Partner

Her first significant public relationship was with Michael Sportes, a fellow entrepreneur. They collaborated on a vintage clothing store in the East Village, Filth Mart, which became a fashionable staple in the New York scene. This relationship, which lasted from 1997 to 2004, predates her major career success on *The Sopranos* and laid the groundwork for her life in the public eye.

Shooter Jennings: The Decade-Long Rocker Romance

The most enduring and defining relationship of Drea de Matteo’s life was with country rocker Shooter Jennings, the son of music legends Waylon Jennings and Jessi Colter. Their relationship began around 2001 and lasted until 2013, though they never officially married. During their time together, they welcomed two children: daughter Alabama Gypsyrose and son Waylon Albert "Blackjack." The couple's commitment to co-parenting has remained strong, even after their separation, which is often noted in media coverage of their family life. Shooter Jennings, a prominent figure in the country and rock music scenes, was a constant fixture in Drea’s life for over a decade.

Michael Devin: The On-Stage Proposal

In a highly publicized moment in 2015, Drea de Matteo became engaged to Michael Devin, the former bassist for the rock band Whitesnake. Devin proposed to her on stage during a Whitesnake concert in Atlantic City, New Jersey, making for a memorable and public declaration of love. Though they were engaged, the relationship eventually ended, and the two did not proceed with marriage.

Who is Drea de Matteo Dating Now? The Latest on Robby Staebler and UVWAYS

The question of Drea de Matteo's current partner has been a source of recent speculation, offering a fresh, current angle for fans. While some older records suggest she might be single, the most recent and compelling reports link her to a new musician, continuing her pattern of dating rockers. The actress is reportedly dating Robby Staebler, the drummer for the psychedelic rock band UVWAYS. Staebler, who is also an artist, has been featured in affectionate photos shared by the actress on social media, leading to the assumption that they are a couple. This relationship, if confirmed, marks a new chapter in her life, following her high-profile engagement to Michael Devin. The pair appear to share a bohemian, artistic sensibility, often pictured in a style that reflects their counter-culture interests. The public's interest in her love life has been amplified by her recent career moves, suggesting that her partners are supportive of her unconventional choices.

The OnlyFans Chapter: How a Financial Crisis Changed Everything

Perhaps the most talked-about aspect of Drea de Matteo’s life in recent years is her decision to join the content creation platform OnlyFans. This move was not a whim but a necessity driven by a severe financial crisis. In interviews, Drea de Matteo has been remarkably open, stating that the platform essentially "saved" her from losing her house and facing bankruptcy. She explained that she was struggling to pay her mortgage and facing significant debt, a shocking revelation for an Emmy-winning actress with a robust career history in shows like *The Sopranos* and *Sons of Anarchy*.

A Newfound Financial Freedom

The transition was immediately lucrative. The actress has been candid about the financial success she has found, claiming she earns "far 'more'" on the adult site than she ever did in her acting career. She has clarified that her content is "sexy" but does not involve explicit sexual acts, focusing instead on artistic and provocative photoshoots.

Controversy and Political Expression

The OnlyFans career has also become a platform for her to express strong, often controversial, political and social views. In one instance, she posed fully nude and covered in paint as a form of protest against geoengineering, an alleged practice she speaks out against. Her discussions about her OnlyFans journey, including appearances on popular podcasts and shows like *Club Random with Bill Maher*, have cemented her status as a figure who is unafraid to challenge conventional Hollywood norms. Her story has sparked a wider conversation about financial instability in the entertainment industry and the shifting landscape of celebrity monetization.

The Enduring Legacy of Drea de Matteo's Unconventional Path

Drea de Matteo's life, both on and off-screen, is characterized by an unapologetic embrace of the unconventional. From her iconic role as the doomed mob girlfriend Adriana La Cerva to her current status as a successful OnlyFans creator and outspoken public figure, she has consistently defied expectations. Her relationship history—a pattern of long-term, committed partnerships with musicians like Shooter Jennings and Michael Devin—shows a deep connection to the rock and roll lifestyle. Today, her rumored connection to Robby Staebler is the latest chapter in a life that is constantly evolving. The financial lifeline provided by OnlyFans has given her a new kind of independence, allowing her to speak her mind and live life on her own terms. Her journey is a compelling blend of Hollywood glamour, financial struggle, and the ultimate triumph of personal resilience, making her one of the most intriguing and talked-about figures in contemporary celebrity culture.