The best books that feel like a romantic comedy from the 1980s—think: Sixteen Candles and Say Anything

The actor John Cusack brought me to this movie, and I read the book after the movie and loved it. One of the key differences between the movie and the book is that the movie is set in Chicago, and the book in North London. As someone who grew up in the ’80s, I started with Cusack as the nerdy sidekick in Sixteen Candles and became obsessed with his Lloyd Dobler character in Say Anything; you know, the guy who dressed in a trench coat and held a boom box over his head outside a girl’s window.

The narrator of this novel is a record shop owner in London named Rob, and he starts off with his desert island, all-time, top five most memorable breakups, in chronological order. When we’re in the record shop that Rob owns, the guys are always making lists: top 5 guitar solos, top 5 horror movies, and so on, and I really enjoyed making up my own lists as if I were in the shop with the guys.

Part of the point of Rob’s Top 5 Break Up is to show the girl who just broke up with him that she’s not even close to the top five. Not too long after he gives us the list of all-time breakups, he goes off to try and visit each woman. All the while this is going on, Rob may or may not get back together with his girlfriend. 

The cover of this book has a stack of mix tapes on it and that’s what got me first: that the writer was going to explain love using the metaphor of a mix tape. As a person who has made hundreds of mix tapes myself—and later burned CDs and after that arranged playlists on Spotify—that the phrase mix tape was in the title was enough for me to pick up the book. Plus, I remember back in the 80s when I sat around waiting for a song to come on the radio so I could record it, and that was how I made my first tapes.

Each chapter in this book starts with an image of a mix tape with the songs listed on it. The writer uses the songs on the tape to write about his relationships. The first chapter ends with this line: “I’m going to be up for a while. Renee’s not done with me yet.” You think maybe the writer is mourning a breakup, but you end up with quite a twist. 

“In walks these three girls in nothing but bathing suits.” That’s how Updike’s story A & P starts, and really, all I’m doing in recommending this book to you is actually recommending that you read the story A & P.

I once became an English major mostly because I was an unconfident student, and both of my parents were English teachers. I figured I could go home and get help with my homework if I needed it. I always say Updike’s A & P is the first story I ever really liked. Later, when I made the English Honor Society in college, I was asked to read a story that was important to me, and I chose this one.

I used to think all stories were old like Beowulf or MacBeth, but this one showed me stories could come from situations I’d lived. After all, I had worked in a grocery store as a teenager and every day I was hoping some cute girls would walk in but they almost never did. Sammy is the name of the kid who works in the A & P and things don’t go so great for him with the girls in this story. 

This is a funny and dramatic book and movie in which Grady Tripp is a university writing teacher who makes a mess out of his relationships. He’s having an affair with the chancellor of the college he teaches at, his wife has moved out maybe for good, and one of the students he has in class and who rents a room from him is attracted to him.

Tripp’s life is like a train wreck you can't stop watching, but also somehow funny. This book also became a great movie of the same name, starring Michael Douglas as the professor, Robert Downey Jr. as his agent, Frances McDormand as the chancellor, and Tobey Maguire and Katie Holmes as students. I mean, c’mon, doesn’t that sound great?!!!

The phrase “girl in a band” in the title got me to pick this book up off a table in the bookstore. I am the kind of guy who will pick up five or so books at a bookstore, take them over to the most comfortable spot I can find, and read the first few pages to see if I want to buy any of them.

The writer Kim Gordon was in an indie post-punk band called Sonic Youth, and I had just barely heard of them. After three years in Sonic Youth, Kim marries one of her fellow band members, and they stay married for 29 years. This book starts when the two of them take the stage together for the last time as they head for divorce and the band's breakup.

“They say when a marriage ends,” Gordon writes on the first pages, “that little things you never noticed before practically make your brain split.” With Gordon standing there on stage wondering what the rest of her life was going to be like once her marriage and her time in the band were over, I was more than up for joining her on the journey in the pages of her book.