If you’ve ever sat down on a rainy Sunday to watch Tom Selleck brooding over a glass of Scotch and a Golden Retriever, you’ve likely stumbled into the world of Paradise, Massachusetts. It's a moody place. But if you're trying to figure out what is the order of the jesse stone movies, you're going to run into a bit of a headache almost immediately.
The production team did something weird right at the start.
They released the first movie in 2005. Then, a year later, they released a prequel that explains how the guy even got to town. If you watch them in the order they aired on CBS, you’re basically starting the book on chapter two. It works, sure, but it’s not the most satisfying way to see Jesse’s slow-burn evolution from a broken LAPD detective to a small-town chief. Honestly, the timeline is everything here.
The Chronological Order: Starting at the Beginning
To see the story play out the way it actually "happened" in the life of Jesse Stone, you have to flip the first two films. Most fans agree this is the superior way to watch. It allows you to meet Jesse while he's still driving across the country with a trunk full of regret and a drinking problem that's barely under control.
✨ Don't miss: Why La Mera Mera Radio is Actually Dominating Local Airwaves Right Now
- Jesse Stone: Night Passage (2006) - Despite coming out second, this is the origin story. We see Jesse arrive in Paradise. He’s been fired from the LAPD for drinking on duty. He meets "Suitcase" Simpson and Molly Crane (played by a pre-superstar Viola Davis).
- Stone Cold (2005) - This was the first one aired, but it takes place after Jesse has already settled into the job. He’s investigating a string of "thrill kills" in the sleepy coastal town.
- Jesse Stone: Death in Paradise (2006) - Jesse starts seeing Dr. Dix (William Devane), a former cop and psychiatrist. This is a huge turning point for his character growth.
- Jesse Stone: Sea Change (2007) - The town council is starting to get on his back. Jesse digs into a cold case from 1992 to keep himself from spiraling.
- Jesse Stone: Thin Ice (2009) - Jesse and Captain Healy (Stephen McHattie) get shot during an unauthorized stakeout. The consequences of this one ripple through the rest of the series.
- Jesse Stone: No Remorse (2010) - Jesse is suspended. He’s basically a private citizen here, consulting on a series of murders in Boston while being forbidden from talking to his own team.
- Jesse Stone: Innocents Lost (2011) - He’s officially out of a job. The council replaced him with a "suit" who doesn't know the first thing about real police work.
- Jesse Stone: Benefit of the Doubt (2012) - A shocking explosion brings Jesse back into the fold. This was the last film to air on CBS before the series moved.
- Jesse Stone: Lost in Paradise (2015) - The "Hallmark" era. It’s a bit different in tone but still features the same grit. Jesse helps the Massachusetts State Police with a serial killer case.
Why the Order Actually Matters
You might think, it's just a detective show, does it really matter? Kinda.
The thing about Robert B. Parker’s character—which Tom Selleck captures perfectly—is that the mystery is usually secondary to Jesse’s internal weather. If you jump around, you miss the subtle progression of his alcoholism and his weird, haunting relationship with his ex-wife, Jenn. In the movies, we never actually see Jenn; she’s just a voice on the phone. This was a deliberate choice by the writers to make Jesse feel more isolated.
If you watch Stone Cold first, you see a man who is already the Chief. You don't see the "why." You don't see the moment the corrupt town council hired him specifically because they thought he’d be a drunk they could control. Watching Night Passage first makes the stakes in the later movies feel way more personal.
🔗 Read more: Why Love Island Season 7 Episode 23 Still Feels Like a Fever Dream
The "Selleck Effect" on the Timeline
It’s worth mentioning that Tom Selleck isn’t just the star; he’s a writer and producer on most of these. Around the fifth movie, Thin Ice, the films stopped being direct adaptations of Parker’s novels. They became "Selleck’s Jesse." This is why the later movies feel more like a continuous character study than a "whodunit" of the week.
The gap between the eighth and ninth movie was three years. Fans thought the series was dead. When Lost in Paradise finally dropped on Hallmark, it felt like catching up with an old friend who had aged a bit, gotten a new dog (Steve replacing the legendary Reggie), but was still fighting the same ghosts.
Taking the Next Step with the Paradise Police
If you’re planning a marathon, my best advice is to grab a bottle of something—maybe not the "black label" stuff Jesse drinks—and clear a weekend. Don’t rush them. These movies are meant to be slow. They’re atmospheric. They’re about the sound of the ocean and the creak of an old house.
💡 You might also like: When Was Kai Cenat Born? What You Didn't Know About His Early Life
Once you’ve finished the nine films, you might be tempted to jump into the books. Just a heads-up: they are different. In the books, Jesse is much younger, and the town of Paradise is a lot bigger. But the soul of the character—the guy who does the right thing even when it costs him everything—is exactly the same.
Your Action Plan for Watching:
- Commit to the Chronological Order. Don't let the 2005/2006 release dates confuse you. Start with Night Passage.
- Pay Attention to the Supporting Cast. Keep an eye on characters like Gino Fish (William Sadler) and Hasty Hathaway (Saul Rubinek). Their arcs span multiple films and show how Jesse’s presence slowly changes the town's power dynamic.
- Check the Streaming Rights. As of 2026, these movies tend to bounce between services like BritBox, Hallmark Movies Now, and Amazon. It's often cheaper to buy the DVD "Complete Collection" if you want to avoid hunting them down every time a licensing deal expires.
The Jesse Stone movies are a rare breed of television where the character is more interesting than the crime. By following the chronological path, you get to see that character built from the ground up.