10 Documentaries for Snowy Evenings

Just what you need after a long night of shoveling.

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Hello, dear readers! It’s been a while, but I’m back this week with some more tips for living your best life. And by best life, I mean curling up in front of your television for a couple of hours to learn about someone else’s life.

There is nothing quite like the experience of watching a well-made documentary, and the documentaries on this list run the gamut from a few that I just discovered on one of our numerous streaming services, to docs that I enjoyed many years ago that have remained lodged in a corner of my brain ever since.


1. Louis Prima: The Wildest

Watch on Amazon Prime

Let’s start with a fun one. This documentary is from 1999, but I just watched it last week. Whenever I hear the question about which entertainer (living or dead) you would want to see perform live, I always immediately think of Louis Prima, Keely Smith, Sam Butera and the Witnesses, and their lounge act that swung hard in Las Vegas clubs throughout the 1950s. I fell in love with Louis Prima’s energetic music some time in high school when I encountered him for the first time on the Mob Hits album. Actually, I first unknowingly encountered him in the Jungle Book, in which he voices King Louis. It was love at first site, and I have dug deeper into his catalog ever since. You can learn more about his legacy in this piece I wrote in 2018 when Keely Smith passed away at age 89.

You can also watch this documentary, which is not the most slickly produced doc you’ll ever see, but features a lot of prime Prima concert footage that I haven’t seen anywhere else. Get ready to tap your feet.


2. Alive and Kicking

Watch on Hulu

As long as we’re in a swingin’ mood, here’s another documentary that I recently found on Hulu. It traces the history of swing dancing—particularly the Lindy Hop—and follows several pairs of professional dancers as they hop around the globe spreading the joy that comes with this exuberant form of dance and competing in various competitions. Come for the mind-blowing dance moves, stay for the heartwarming stories and the interviews with some of the legends of Lindy Hop who were still alive when this doc was produced in 2016.


3. Three Identical Strangers

Watch on Hulu

Imagine you had a twin that you didn’t know about, and you met him when you started school at a new college that he just happened to attend and everyone thought you were him. Now imagine that your story winds up in the newspaper, and a third guy steps forward and realizes that he is your triplet. Identical triplets separated at birth! Thus is the unbelievable premise of this true (and truly sad) story that unfolds in riveting and well-produced fashion.


4. McMillions

And speaking of crazy stories, it doesn’t get much crazier than this multi-part rollercoaster ride documentary about the secret cheating scandal behind the McDonald’s Monopoly game. This documentary gets special recognition for its use of reenactment, its engaging storytelling sources (especially a wacky FBI agent who seems like a fictional character), and its instant 90s nostalgia factor. I don’t want to give any other details because this one really needs to be experienced firsthand. It’s definitely one of my favorites on this list, and my wife and I had to keep starting the next episode after finishing each cliffhanger—and sometimes we just ended up watching another full episode.


5. The Staircase

This true-crime documentary is by far the darkest one on the list, as the series tells the story of a novelist who called paramedics when his wife fell down the stairs, but was ultimately arrested and charged with her murder. Apparently this one came out several years ago and was one of the first true-crime docs of its kind, but the 2018 Netflix re-release added new chapters with additional information and an updated ending. The twists and turns never end, and—like so many true-crime documentaries of late—you probably still won’t know what to think after you finish it.


6. Confessions of a Superhero

Watch on Amazon

OK, this one goes way back. I remember watching it on Hulu when Hulu first came out and I got a special invite to join this funky new service that let me watch a bunch of movies and TV shows for free. There weren’t even any ads on the platform yet, can you imagine?! I tried this documentary and—though I don’t remember many details—I know I really enjoyed the concept and the intriguing characters the documentary profiles. While the lives of these people who patrol Hollywood Boulevard dressed in superhero costumes taking photos for tips are ultimately sad, there is a lot of humor in the documentary as well.


7. Won’t You Be My Neighbor?

Watch on Amazon (currently free with ads if you’re not a Prime subscriber!)

Speaking of people who pretend for a living, here’s another must-see documentary that was released in theaters in 2018. Fred Rogers is among the greatest human beings who ever walked the earth, and this documentary does tremendous justice to his work and legacy. This one definitely brought on some tears, and one of the lines quoted in the trailer never fails to give me chills. “Love is at the root of everything. Love or the lack of it.” Godspeed, Mr. Rogers.


8. It All Begins With A Song

Watch on Amazon

This documentary is an in-depth look at the songwriting scene in Nashville and was truly eye-opening about the songwriter’s process and day-to-day life as well as the fact that there are so many unsung (no pun intended) songwriters who have written very famous songs but are still living lives of quiet songwriting desperation and working odd jobs in Nashville to pay the bills. I love documentaries that immerse you in a culture you wouldn’t otherwise experience, and this one does an excellent job of that.


9. This Old Cub

Watch on Amazon

If Louis Prima is the entertainer I would most like to watch live, Ron Santo is the Chicago Cub that I wish I would want to see play at Wrigley Field. I love this documentary and the humorous, raw portrayal of a man who loved the game and loved his team, perhaps more than anyone who ever played baseball. After listening to him broadcast so many Cubs games, I already felt like I knew him, and this documentary was a welcome trip into his world and the sunny attitude he maintained, despite facing obstacles as a diabetic athlete and later in life as the disease took his legs and ultimately his life.


10. The Last Dance

Watch on Netflix

Yeah, I’m sure you’ve heard of this one. But no documentary list by a guy who grew up in the Bulls championship heyday would be complete without a nod to this epic masterpiece. Say what you will about the director’s kowtowing to Jordan’s editing whims, but the experience of watching this documentary took me back to a time when basketball was magical and MJ was a master wizard. (Well, he was a Bull. He was a Wizard later, but you know what I mean.) The interviews, the archival game footage, and the behind-the-scenes team intrigue all combine to make this one of the greatest documentaries I’ve ever seen. I lived through it as a child, but I still learned so much, and I already want to watch it again!


If you have a suggestion for an awesome/thought-provoking/entertaining documentary that you saw recently, leave a comment! I’m always on the lookout for more, and the Chicago winter has only just begun—plenty of time for more snowy evenings in our future. Thanks for reading and please pass this along to anyone who might enjoy it.

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