I recently viewed the seven-part series Escape at Dannemora, a Showtime project directed by Ben Stiller and starring Benicio Del Toro as prisoner Richard Matt, Paul Dano as prisoner David Sweat, and Patricia Arquette as prison employee and accomplice Tilly Mitchell. This series for mature audiences tells the story of these two prisoners who escaped during the summer of 2015 from the Clinton County Correctional Facility in Dannemora, near the Canadian border in upstate New York. Overall, I enjoyed the series — though at times, it felt a bit drawn out — but the one aspect that really piqued my interest was the use of the flashbacks in episode six. Initially, I thought the flashbacks were unnecessary because I was anxious to proceed with the main storyline. However, by the next day, and before I watched episode seven, I realized the flashbacks were definitely necessary and definitely served a valuable purpose.
During the first five episodes of this series, we meet the prisoners and the female employee who facilitated their escape. We identify somewhat with Matt and Sweat because they seem hardworking and likeable. Both are housed in an honor unit within the prison, which means they are well behaved, and, as a result, they merit specials privileges within their cells: access to television, music, food, and even art supplies. Matt is a painter, and he is teaching Sweat to become an illustrator. In addition, they both work every day in the sewing shop. As viewers, we know they must have done something wrong to find themselves in prison, but we sympathize with their confinement, and we want to see them escape.
We also empathize with Mitchell because she seems confined to a prison of her own. She is the supervisor of the sewing shop, one of the few female employees in the prison, and she appears to be trapped in a failed marriage. Her husband also works at the prison, but the romance has escaped their marriage, and she is looking for an escape as well. Consequently, she manages to have an affair with Sweat, and after he is transferred to another job, she has an affair with Matt. Both affairs appear to be purely physical for the prisoners, but they mean much more to Mitchell. Thus, when Matt suggests that the three of them escape and go to Mexico, she is more than willing to assist in the operation. And amazingly, the plan works — until it doesn’t.
The two prisoners manage to escape from their cells, and they find themselves outside the prison walls at midnight at the precise location where Mitchell was supposed to meet them with her car. At that point, they should have had a five-hour head start before anyone would notice their absence, a head start that should have put them 300 miles or so away from Dannemora. Unfortunately for them, the flashbacks begin, and their plans go astray.
Without giving away too much about what goes wrong, Mitchell, who was all packed and ready to flee to Mexico, couldn’t quite bring herself and her car to the rendezvous point. She remembers all too well a key experience in her life, and she decides she can’t escape after all.
The two prisoners, meanwhile, have nothing to prevent them from fleeing, but the movie’s flashbacks provide the details about why they were imprisoned in the first place. Those flashbacks remind the viewers that these cons are not innocent victims; they are not at all like Andy Dufresne, a banker wrongly convicted for a double murder in the 1994 movie The Shawshank Redemption, a movie based on Stephen King’s novel. No, these two prisoners are real-life convicted murderers, and their crimes come vividly to life in the flashbacks. Thus, as viewers, our allegiances change. Instead of rooting for these prisoners to make it all the way to the Baja Peninsula, we switch sides and transfer our allegiance to the local police and the state troopers who will try to track them down.
Flashbacks, of course, have been around forever. In the Old Testament, for instance, God split the Red Sea to allow the Israelites to escape from the Egyptians. Yet, afterwards, the Israelites struggled at times and worried that leaving Egypt was a mistake, so Moses used a flashback to remind them of God’s provision: “Remember that you were slaves in Egypt and that the Lord your God brought you out of there with a mighty hand and an outstretched arm” (Deuteronomy 5:15 NIV).
Through the centuries since then, storytellers have often used flashbacks to explain why characters act in a certain way — why, for example, Matt and Sweat committed their crimes — or fail to act, as Mitchell failed to act at her decisive moment. Thus, if you feel your readers or viewers will be puzzled or confused by a character’s actions, you may want to use a flashback or two to help explain that character’s motivation.