I was first introduced to Mike Leonard not through his work on The Today Show, but through his “appearance” as the father on The Brendan Leonard Show in 2003. The show itself was nothing short of a miracle, a teenager given complete creative freedom to provide forty episodes of content, the set his backyard, the cast his friends, the crew his relatives, the production company owned by his father two blocks from their house. That close-knit family appeal was fascinating to watch. And Mike Leonard’s work on The Today Show was all about slices of life, finding interesting things in weird places, finding friends in all corners of the world. Combine those two together and you have The Ride of Our Lives, the story of how Mike Leonard took three of his kids (and one daughter-in-law) and his aging parents in two RVs across the country for one last cool road trip. Spoilers to follow…

The trip starts picking up the Leonard grandparents, Marge and Jack (also known as Moose and Spoose), at their new home in Phoenix, aiming to see some sights around the country in three weeks and end up in Chicago in time for the birth of their first great-grandchild. (It should be noted that while this is a vacation, Mike never goes anywhere without a camera, and since two of his children, Matt and Kerry, are part of his production company, they do film a large portion of the trip, which ended up as a miniseries on The Today Show. This is worth noting if only for the fact that it only comes up once, during the latter half of the book, and it is slightly jarring.) The book itself isn’t so much the solitary tale of the Leonards’ adventure(s), but is also peppered with tales of the Leonards themselves. Such interludes include:
– Mike secretly dating his future wife Cathy in high school (she did not think he was cool (he was not); he was afraid his brothers would make fun of him for dating (they did)).
– Tales of “boys being boys” from Mike’s childhood, like his brother putting a turtle in his mouth, or a neighborhood kid getting his neck sliced from ear to ear by an unmarked strung wire while riding his bike. (This story was disturbing beyond all reason because it is basically one of my worst nightmares, and it’s played off like “welp, crap happens” since the kid lives. Meanwhile, I’m frantically trying to avert my eyes. Uncool, book, uncool.)
– Stories of daughter Megan’s childhood, such as the time she violently threw up in the back seat during a test drive, forcing her parents to go home with a new station wagon sans new car smell.

Some of these stories are authored by Mike, some are recounted in dialogue whilst trapped in the RV. And you can see where Mike gets his spur of the moment, stream of consciousness style, because the tales the Leonards tell one another are only ever prompted by the vaguest thought or conversational thread. It’s an entire book of “hey, do you remember that time..?” You might chalk it up to old age when done by Jack and Madge, but then you realize it’s a clear family trait. As it stands, it would be kind of irritating, like listening in on someone’s inside jokes, if they weren’t all explained into detail. Because of that, you feel like you’re a part of the trip.

(Speaking of family traits… Jack Leonard has this incredible habit to translate any situation into a musical interlude of a weird old song no one has ever heard. His family is often confused by this: both the action of it, and the weird little songs themselves. It says a lot about my own childhood that I found this the most relatable part of this book. Hi, Mom.)

The journey takes them around to the Alamo, to the Biltmore estate in Asheville, North Carolina, to the now-decaying Paterson, New Jersey, where Jack and Madge once grew up. Mike has friends he made doing Today Show pieces, so he sets up little adventures along the way, touring hip-hop recording studios and letting the good times roll with a crazy Louisiana man who is listen in the phone book as Crip. He admits that he sets these up for the amusement of giving his folks a little culture shock. It never comes across as mean-spirited, which is a relief, but it does set an interesting tone that this ride of their lives isn’t entirely sentimental and schlocky. It may be a last hurrah, Mike knows deep down, but they aren’t dying tomorrow and he won’t let their age define their entire existence, even if he uses the gap to give his own kids some moments of levity. (This forced culture shock occasionally gets turned on its head, such as when the hip-hop producer firmly decrees that eighty-seven-year-old Jack Leonard, who abhors the sideways/backwards ballcap trend, to be cool when he rolls into the studio wearing a Kangol.)

One of the main themes of the book is perseverance. Mike is all too willing to admit his many failures and shortcomings, and is often the first to take well meaning potshots at himself. He knows his weaknesses and he knows his skills. One of his main skills is to just keep moving forward, to not get too mired in his failings, and to try and learn from the experience, to just keep plugging away.

The other main theme is less about the internal factors that drive our life, and more of the external. More specifically, the tiny connections that are made throughout life, and how sometimes those tiny connections can form large portions of our future. Such as Mike’s great-grandmother passing a ring down through the family, that gets transported to Mike via a kind stewardess (it was the seventies), so he can propose to his girlfriend Cathy. He then uses the money he would’ve spent on a ring to buy a new video camera, and then the rest is history. This trip, the job that gave him the time and money to take it, not to mention the career that made him so many connections and friends to pepper the trip with all of its weird little sidebars and experiences, all the result of the ring of a woman he’d never known and the kind nature of a flight attendant he’d never met.

Let me be frank, this is not the most eloquently written book I’ve ever read, and if I hadn’t been watching a cable channel one summer afternoon a decade ago, I might never have known about the existence of Mike Leonard and never picked up the book. But it is a charming story, and a positive method, and my own experiences leading up to reading the book itself are exactly what Mike is talking about: weird coincidences, tiny things that can change your life in big or small ways. It really emphasizes the beautiful, weird, terrifying interconnectedness of the world in a wonderful way.