The Texas oil fields may be chaotic on-screen, but the real-life relationships of the Landman Season 2 cast are just as gripping. From whirlwind marriages and headline-making divorces to long-lasting love stories and closely guarded romances, the personal lives of these stars offer a compelling look into what happens when the cameras stop rolling. Here’s a deep dive into who’s single, married, divorced, or still figuring it out.
Billy Bob Thornton: Hollywood’s Most Talked-About Romantic Past
Billy Bob Thornton's relationship history reads like a Hollywood drama in itself. With six marriages behind him, Thornton’s journey has been anything but ordinary. His first marriage to Melissa Lee Gatlin in 1978 produced a daughter, Amanda Brumfield, whose 2009 conviction for aggravated manslaughter made headlines.
Following that, Thornton married Toni Lawrence in 1986, then Cynda Williams in 1990, though both unions ended in divorce with little public information. His fourth marriage to Pietra Dawn Cherniak brought two sons, William and Harry, but also ended by 1997.
Thornton’s most infamous relationship came next—his whirlwind 2000 marriage to Angelina Jolie, just after ending his engagement to Laura Dern. Their edgy romance, including wearing vials of each other’s blood, became pop culture legend. They even adopted a son, Maddox, before divorcing in 2003.
Currently, Thornton is settled with Connie Angland, whom he married in 2014 after a decade-long relationship. Together, they share a daughter, Bella, and regularly appear together on red carpets and at sporting events.
Demi Moore: Love, Loss, and Reinvention
Demi Moore’s romantic life has been a staple of public fascination for decades. Her first marriage was to musician Freddy Moore from 1981 to 1985, a relationship she has since reflected on with candor in her memoir.
Her second marriage to Bruce Willis was iconic. The couple wed in 1987, had three daughters—Rumer, Scout, and Tallulah—and maintained a close friendship even after their 2000 divorce. Moore has publicly supported Willis through his health struggles, highlighting the enduring bond between them.
Moore’s third marriage to Ashton Kutcher, 15 years her junior, was rocky. The couple tied the knot in 2005 but separated in 2011 after reports of infidelity and substance abuse issues surfaced. Their divorce was finalized in 2013. Now single, Moore continues to thrive professionally, recently winning acclaim for her role in The Substance (2024).
Michelle Randolph: A Private Heartbreak
At 27, Michelle Randolph is currently single. She dated actor Gregg Sulkin, known for his Disney Channel fame, for five years before the two quietly split in 2023. Neither has shared the reason for the breakup, but they’ve remained out of the spotlight since.
Fun trivia: Randolph’s sister, Cassie, was the winner of The Bachelor Season 23.
Jon Hamm: Late Blooming Romance
Jon Hamm, long known for his bachelor lifestyle, found lasting love later in life. He met actress Anna Osceola on the set of Mad Men in 2015 and began dating her in 2020. The couple married in 2023.
Hamm has spoken openly about the comfort and emotional depth marriage brings, describing their relationship as a source of stability and joy. The couple frequently appears together on red carpets, though they don’t have children.
Ali Larter: A Quiet Family Life
Ali Larter’s off-screen life is a contrast to the drama of her character. Married to actor Hayes MacArthur since 2009, the couple has two children and lives in scenic Idaho.
Larter has often praised their peaceful mountain lifestyle and the strong sense of community they’ve found. The couple occasionally shares glimpses of their family life on social media and is known for their red-carpet appearances.
Kayla Wallace: On-Set Romance Turned Real
Kayla Wallace found love where many actors do—on set. She met her husband, actor Kevin McGarry, while filming When Calls the Heart in 2018. After several years of dating, they got engaged in 2022 and married in 2024.
The couple has adopted a dog and often shares sweet moments on Instagram, though they tend to keep relationship details private during interviews.
Mark Collie: A Love Story That Endures
Country singer and actor Mark Collie has been married twice. His first marriage to Anne Collie ended in 2001. In 2009, he wed Tammy Stewart, and they’ve been inseparable since.
Collie regularly posts heartfelt tributes to Tammy on social media. Though the couple doesn’t have children, their affection for one another is undeniable.
James Jordan: A Love Kept Mostly in the Shadows
James Jordan is one of the more private cast members. He’s married to Debra Schrey, and while he occasionally shares touching posts about her, the couple has kept the details of their love story—such as when and how they met—under wraps.
What we do know is that Jordan credits his wife with grounding him through his ups and downs.
Colm Feore: Long-Lasting Love Off the Grid
Veteran actor Colm Feore has also been married twice. His first marriage to Sidonie Boll produced a son, Jack, before ending in 1994. That same year, he married choreographer Donna Feore, and they’ve been together ever since.
The couple has two children and lives largely outside the limelight, though they occasionally attend public events together.
The cast of Landman Season 2 proves that real-life relationships can be just as dramatic—and heartwarming—as those depicted on screen. From longtime love to tumultuous pasts and fresh beginnings, each star brings a unique story to the table. Whether married, single, or somewhere in between, these actors show that life off-camera can be just as compelling as the scenes they bring to life.
