10 best true crime documentaries like ‘Jailbreak: Love on the Run’
When Jailbreak: Love on the Run debuted on Netflix, it quickly landed in the Top 10. The documentary explored the unlikely relationship that developed between Vicky White, a corrections officer, and Casey White, an inmate. Their problematic romance prompted Vicky to make terrible decisions, ultimately breaking Casey out of prison and going on the run with him.
Unsurprisingly, the situation ended badly. But for true crime fans looking for similar stories of love, obsession, and tragedy, the following 10 documentaries are sure to fit the bill.
Lover, Stalker, Killer
One of the things that is so compelling about Jailbreak: Love on the Run is seeing the extent of what Vicky was willing to do because of her obsessive love for Casey. Another Netflix documentary—Lover, Stalker, Killer—features similar themes.
Lover, Stalker, Killer reveals the story of a love triangle that turned deadly. Newly single man David Kroupa took a chance on dating sites and eventually found himself torn between two women, Liz Golyar and Cari Farver. But when the two women finally cross paths, everything goes to hell. Cari seemingly launches an offensive against Liz, and her violent behavior continues to escalate. The documentary culminates in a shocking and tragic twist that spotlights how dangerous obsession can be.
I Love You Now Die: The Commonwealth v. Michelle Carter
This two-part docuseries details a case from Massachusetts where a romance between two high schoolers went horribly wrong. Michelle Carter and Conrad Roy’s strange relationship culminated in Conrad’s suicide. However, the case presented a difficult legal quandary, because though Michelle was miles away from Conrad when he killed himself, her barrage of texts encouraging him to go through with his plans.
I Love You Now Die examines the case from both sides, the prosecution and the defense, and viewers see the extend of Michelle’s manipulation as well as her own fractured psyche and mental health problems. It was a complex and tragic situation, and the docuseries does a good job capturing what made this case unique.
Bad Vegan: Fame. Fraud. Fugitives.
Many Jailbreak viewers are split on who was the real manipulator, Casey or Vicky. In a similar docuseries, Bad Vegan: Fame. Fraud. Fugitives., there is less ambiguity. The docuseries follows the rise of vegan restauranteur, Sarma Melngailis, and details how her life was derailed after falling for a conman named Shane Fox (real name Anthony Strangis).
Through extensive interviews with Sarma, the docuseries details the series of wild claims and promises that Anthony made, which Sarma bafflingly believed. Anthony claimed to be a “higher being” who could make Sarma’s beloved dog, Leon, immortal. While most people would quickly clock Anthony’s lies, Sarma went along with him. Sarma ran her restaurant into the ground by continuously siphoning money to Anthony, screwing over most of her employees in the process.
Mommy Dead and Dearest
Gypsy Rose Blanchard got a lot of press after her release from prison in December 2023, but Mommy Dead and Dearest is the best documentary about the harrowing childhood Gypsy endured and the horrific murder that sent her to prison. In a story of love gone wrong, Gypsy, living under her mother Dee Dee’s strict control, connected online with a mentally unstable young man. Together, the young couple plotted Dee Dee’s murder as a way to free Gypsy.
This case is particularly interesting because of how toxic and abusive Dee Dee was. The HBO documentary details the scam Gypsy’s mother perpetuated by pretending her daughter was a sick and disabled child, and shed light on Dee Dee’s controlling behavior. Gypsy may have responded in the extreme, but Dee Dee was far from innocent.
Dear Zachary: A Letter to a Son About His Father
Probably the most tragic documentary on this list, Dear Zachary: A Letter to a Son About His Father artfully tells a story that ends with an emotional gut punch you won’t see coming. Filmmaker Kurt Kuenne embarked on Dear Zachary as a memorial for his friend, Andrew Bagby. Andrew was shot and killed by his ex-girlfriend, Shirley Jane Turner, after he dumped her, and Kurt saw this film as a way to preserve Andrew’s memory.
But when Shirley revealed that she was pregnant with Andrew’s child, the purpose of the documentary changed. Kurt retooled his film as a way for Andrew’s newborn son, Zachary, to know the father he would never get to meet. Unfortunately, the situation took a much darker turn, and the documentary now stands as a testament to how many lives one unstable person can destroy,
The Tinder Swindler
Another documentary that explores the dangers of romantic manipulation is The Tinder Swindler. Multiple women interviewed for this documentary speak of their experiences with an Israeli scammer going by the name Simon Leviev. These women met Simon on Tinder, and that’s where their lives went drastically downhill.
Like Vicky White, the women of this documentary were convinced to make decisions that would have a profound impact on their lives. Simon ran a Ponzi scheme, where he would seduce his marks, posing as an ultra wealthy high roller. He eventually convinced them to send him large amounts of cash to help him in an “emergency” situation. Simon then used that money to target a new mark and start the cycle over.
Tell Them You Love Me
If the unequal power dynamics in Jailbreak were of interest to you, Tell Them You Love Me raises similar questions. The documentary tracks the story of former professor Anna Stubblefield, whose questionable relationship with Derrick Johnson, a nonverbal man with cerebral palsy, led to a sexual assault conviction.
Though Anna maintains the emotional and sexual relationship between her and Derrick was consensual, many others, including Derrick’s mother, insist that Derrick is unable to consent to such a relationship. It’s a complex issue, and the documentary explores several points of view, though it’s up to viewers to make their own decisions.
Jodi Arias: An American Murder Mystery
Jodi Arias made headlines when she was arrested, and later went to trial, for the murder of her boyfriend, Travis Alexander. After Travis was found dead in his shower, it didn’t take authorities long to narrow in on Jodi. But even after her arrest, Jodi’s bizarre behavior and claims did nothing to convince anyone of her innocence. The three-part docuseries, Jodi Arias: An American Murder Mystery, details the background of the case, the crime, and Jodi’s ever-changing stories about what actually happened.
Because Jailbreak subject Vicky died before being apprehended, there was no trial for her crimes. However, if she had, one wonders if her trial would have been similar to Jodi’s. After all, Jodi was similarly motivated by obsession, and Vicky might have scrambled to find a defense, just as Jodi did.
Perfect Wife: The Mysterious Disappearance of Sherri Papini
Perfect Wife: The Mysterious Disappearance of Sherri Papini is a docuseries that discusses a truly baffling kidnapping hoax. When Sherri Papini was found in November 2016 after a three-week disappearance, everyone initially thought she survived a horrifying ordeal. But it wasn’t long before the inconsistencies in her story raised major questions with investigators.
The truth of what happened to Sherri is absolutely wild, and it’s hard to imagine what she was thinking. Like Vicky in Jailbreak, this docuseries leaves viewers wondering how and why Sherri did what she did. However, there’s no rational explanation for the actions of an irrational person. In this way, Vicky and Sherri could be two deluded peas in a pod.
Killer Sally
Another tragic case of romance gone very wrong is detailed in the docuseries Killer Sally. In 1995, Sally McNeil shot and killed her husband, Ray McNeil. Though she claims it was in self defense, there are differing opinions about whether that’s true.
Many true crime fans have doubts because Sally was a bodybuilder with a history of aggression and jealousy (though Ray was also a bodybuilder and considerably stronger than Sally). Due to the details about Sally and Ray’s toxic and abusive marriage, the entire situation is pretty murky, and it’s hard to determine to what extent Sally was acting in self defense.
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