Inside the ‘Landman’ Cast’s Real-Life Love Stories: Engagements, Marriages & Sweet Romances
The stars bringing Texas oil drama to life have their own swoonworthy relationships off screen
Everyone knows that Taylor Sheridan’s hit TV show Landman is filled with swoonworthy love stories, and it seems as though the cast members also have sweet romance in their lives! Read on for the details on the real-life couples of Landman, from the newly engaged to the happily married and more.
James Jordan: engaged and loving it
James Jordan hasn’t been shy about showing his love for Debra Schrey on social media, and his recent post is no exception! In a newly updated post, he shared that they got engaged after several years of dating.
“She said yes! We’re up in Santa Ynez celebrating. Thanks to the folks at Matties Inn in Los Olivos for helping make it a surprise, and the crew @barlecote for making a great dinner,” the caption read. “We’re so happy!”
Jordan and Schrey don’t have any children and there is no word on when they will officially tie the knot.
Billy Bob Thornton’s wild relationship history
Billy Bob Thornton has been married six times. First to Melissa Lee Gatlin, whom he was with from 1978 until 1980. Their daughter, Amanda Brumfield, was sentenced to 20 years in prison in 2009 for aggravated manslaughter of a child and aggravated child abuse.
Then, in 1986, Thornton married Toni Lawrence and remained with her until 1988, but details of their time together remain a mystery.
The actor married Cynda Williams two years later and stayed with her until 1992. Just like his second wife, though, the details of this relationship are veryunclear.
Next came Pietra Dawn Cherniak, whom Thornton married in 1993. During that time, the duo welcomed two sons, William Langston Thornton and Harry James Thornton, in June 1993 and June 1994, respectively. Thornton and Cherniak went their separate ways in 1997.
Thornton’s fifth and most talked-about marriage was in 2000, when he married Angelina Jolie—whom he met on the set of Pushing Tin (1999)—shortly after ending his engagement to Laura Dern. Following their nuptials, the two quickly made headlines after they were spotted wearing vials of each other’s blood around their necks. Jolie also famously got Thornton’s name tattooed on her arm, but covered it up after their split.
“The necklaces were a very simple thing, ‘Hey let’s poke our fingers with a pen and smear a little blood on there and when we’re away from each other we’ll wear the necklace,’” Thornton said, per PEOPLE. “It was that easy. But by the time it came out in the press, it sounded like we were wearing a bucket of blood around our necks.”
In 2002, they adopted son Maddox from Cambodia, and after their divorce in 2003, Jolie got full custody. The two remain friends to this day.
“Angie is still a friend of mine. She’s a great person and she’s done so much,” the actor said. “She makes movies that are important to her; whether they succeed or fail, she still does what she believes in, and I’ll always respect her for that.”
Finally, in 2014, Thornton married Connie Angland after 10 years of dating and has been with her ever since. In 2004, they welcomed their daughter, Bella.
“We [got married] for her, really,” Thornton said on The Late Late Show with James Corden in 2015. “Because after a while, it was like, ‘Why aren’t my mommy and daddy married after 10 years?’”
Thornton and Angland often walk various red carpets together or sit courtside at sporting events.
Demi Moore’s life after Bruce and Ashton
You may remember some of the men Demi Moore—nee Guynes—has married. First, there was musician Freddy Moore from 1981 to 1985. Following their split, Moore kept her married name.
“The night before we got married, instead of working on my vows, I was calling a guy I’d met on a movie set,” the actress revealed in her 2019 memoir Inside Out. “I snuck out of my own bachelorette party and went to his apartment. Why did I do that? Why didn’t I go and see the man I was committing to spend the rest of my life with to express my doubts? Because I couldn’t face the fact that I was getting married to distract myself from grieving the death of my father. Because I felt there was no room to question what I’d already put in motion. I couldn’t get out of the marriage, but I could sabotage it.”
Following her split from Freddy, Moore married Bruce Willis in 1987, after four months of dating. They welcomed three children together—Rumer, Scout and Tallulah Belle Willis—before divorcing in 2000. The two remain friends to this day, and Moore has often spoken publicly about Willis’ aphasia.
“Given the givens, he’s in a very stable place at the moment,” Moore said in December 2024, per CNN. “And I’ve shared this before, but I really mean this so sincerely: It’s so important for anybody who’s dealing with this to really meet them where they’re at. And from that place, there is such loving and joy.”
Moore’s third marriage was to Ashton Kutcher from 2005 until 2013. She is 15 years older than him. They split after 10 years, citing Kutcher’s infidelity and her drug and alcohol problems.
“It is with great sadness and a heavy heart that I have decided to end my six-year marriage to Ashton,” Moore said in 2011. “As a woman, a mother and a wife, there are certain values and vows that I hold sacred, and it is in this spirit that I have chosen to move forward with my life.”
The actress is now single and just won her first-ever film award for her role in The Substance (2024).
Michelle Randolph’s breakup with Disney star Gregg Sulkin
At age 27, actress Michelle Randolph is single and has been since her breakup with actor Gregg Sulkin (best known for playing Mason Greybeck in Disney Channel’s Wizards of Waverly Place) in 2023. The two were together for five years, and the reason for their split remains unknown.
Randolph is now reportedly dating actor Glen Powell, and according to a source close to the couple they “started seeing where things would go around October and have been trying to keep it under the radar for almost two months now.”
Fun fact about Randolph: Her sister Cassie appeared on Colton Underwood’s season of The Bachelor in 2019 and even won, but they went their separate ways shortly after filming wrapped.
Jon Hamm’s real-life romance with Anna Osceola
In 2023, award-winning actor Jon Hamm married for the first time. He met Anna Osceola in 2015 on the set of Mad Men, but they didn’t begin dating until 2020.
“Ideally, it gives you and your partner a sense of stability and comfort and an identifying capacity that is better, deeper, richer, than ‘it’s my girlfriend’ or ‘my boyfriend’ or what have you,” the actor said on the iHeartRadio’s Table for Two podcast, hosted by Bruce Bozzi, in 2023. “It’s exciting because it’s all potential, it’s all possibility and it’s all positive.“
The couple don’t have children, but they do walk red carpets together all the time.
Ali Larter and her quiet life in Idaho
Unlike her onscreen husband, Thornton, actress Ali Larter has only been married once. In 2009, she and Hayes MacArthur tied the knot. Since then, they have welcomed two kids together and currently live in Idaho.
“We fell in love with the beauty of the mountains and their quiet grandness,” Larter told Rue Magazine in September 2024. “People look out for each other. There’s a real sense of community here, and we’re so happy to be a part of it.”
Larter is 49 years old and her husband is 47. They frequently walk red carpets together and sometimes share fun videos of their life in Idaho on social media.
Kayla Wallace found love on set—and now she’s married!
Kayla Wallace met her husband, Kevin McGarry, while filming When Calls the Heart Season 6 in 2018. They got engaged in December 2022 and said “I do” in September 2024. They have since adopted a dog.
The two do post about each other quite a bit on Instagram, but have remained tight-lipped about the details of their relationship in interviews.
Mark Collie’s sweet second marriage will melt your heart
Actor and country music star Mark Collie has been married twice in his career, first to Anne Collie from 1982 until 2001. Then, in 2009, he married Tammy Stewart and has been with her ever since.
“Happy Birthday to the love of my life, Tammy Stewart Collie. I simply couldn’t do life without you, baby. I wish you love, laughter and an abundance of buttercream icing on your special day,” Collie wrote on Facebook in 2021. “I love you with all that I am.”
Colm Feore: Married twice—but out of the spotlight
Like many of his Landman costars, Colm Feore has been married multiple times. First, he was wed to Sidonie Boll from 1983 until 1994. During their time together, the two welcomed a son named Jack, but other details on the relationship remain unknown.
Later in 1994, Feore married Donna Feore and has been with her ever since. They have welcomed two kids together, and while they prefer to keep their private life private, they have walked red carpets together.
Sam Elliott: Married for decades
Actor Sam Elliott has been married to his wife Katharine Ross since 1984. They have one daughter together and are often seen walking red carpets one another.
“I think really what it boils down to is we love each other, and we work at it. And I think more importantly than anything, it takes wanting to be married,” Elliott told NPR in 2017. “The two things that I wanted in my life were to have a movie career and to be married, to have a family. And it’s an embarrassment of riches that I’ve got both.”
Andy Garcia: In love with many children
Andy Garcia has been married to his wife Marivi Lorido Garcia since 1982. They have four children together, and according to their daughter Alessandra there favorite family spot is Disneyland.
“For Mother’s Day, we’d always take the opportunity to go to Disney,” she told Vogue in 2020. “[Marivi is] a huge fan and a member of Club 33, their secret private club.”
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