100 Books Like Skippy Dies

I am recommending this work of fiction selected by The Compassionate Friends Sibling Grief Book Club. Ann, with grace, handles not only the sibling loss of a brother, a boy the sole survivor of a plane crash, but the depth and breadth of grief from the aunt and uncle Edward lives with. Edward’s aunt grieving the loss of an unborn child and her sister, says to Edward, “You’re not okay. We are not okay. This is not okay.” I’m certain other bereaved siblings can relate, “he mourns what his brother has lost.” I related to how in a family we handle grief differently and often are unable to communicate how we are feeling. 

Edisto was the first coming-of-age novel I fell in love with as an adult reader and the book that showed me the tremendous literary potential of the genre. Padgett Powell endows his protagonist, twelve-year-old Simons, with what comes across as precociousness, but in fact reflects the depth of thinking that many young tweens and teens have. Simons wrestles with his narcissistic parents’ competing visions of his future—although neither bothers to ask him what he wants—while hanging out on the sultry island of Edisto off the coast of South Carolina with an enigmatic older acquaintance, Taurus, who offers him tastes of adult life and the kind of attention his parents are incapable of providing. Powell’s deft prose and realistic dialogue make it all fully believable, and at times riotously funny. Edisto is nothing short of brilliant.

You’re fifteen years old, living unhappily with your feckless parents and unstable older sister in a small town in Montana. And then your family implodes: your parents are arrested for bank robbery and your sister flees to parts unknown. As troubling as the premise is, Canada becomes even darker and more ominous as young Dell Parsons travels alone to Saskatchewan to live with erstwhile family friends, but in fact enters a whole new world of intrigue and violence. Dell is a stoic character, and you desperately want to see his life take a turn for the better. What you get instead is a case study in resiliency and survival. Ford’s prose is powerful; every word counts, every sentence pulls you deeper into the story.

Bruiser is only nine years old, younger than most “coming of age” protagonists, but his anxiety-ridden family life in a Manhattan apartment has aged him. His father is a philanderer who rarely is home and often physically abusive when he is; his mother is a deeply depressed poet. Bruiser spends most of his time running around his Upper West Side neighborhood with a make-shift gang of older boys—and has the bruises to show for it, hence his nickname—or hiding at the bottom of the clothes hamper when his parents are going at it. He befriends a 10-year-old girl, Darla, who lives across the courtyard with her drug-addled mother and who convinces him to run away with her. Their journey, which takes them first to West Virginia in search of Darla’s father and eventually to North Carolina, is the book’s magic. Both kids are pre-puberty, so it’s… show more.

Sebastian Dangerfield, a scruffy Yank studying at Trinity College Dublin under the GI Bill, loses his wife, finds a lover, and talks to himself–“In my heart where no one else can hear me.”

The book was banned for decades after publication in the 1950s, not so much for indecency (though there is that) as for sheer insolence. The Irish writer Sean O’Reilly asks: “Is there, even after all this time, something risky, illicit perhaps, about Sebastian Dangerfield whispering in your ear while your heart is bursting with laughter?"

Another 1950s anti-hero in the same gang as Holden Caulfield and Jake Donaghue. Another bad example for my guidance.

This book has one of the most unique premises I’ve ever come across in any book, much less a romance—Tiffy is just out of a toxic relationship and needs a cheap apartment fast. Leon is a palliative care nurse who is working graveyard shifts and needs extra money to help his brother. They come to an agreement—without ever actually meeting each other—to split the flat: Tiffy is there while Leon works and vice versa. 

They begin to communicate through Post-it notes, and it’s honestly the most beautiful development of a relationship I’ve ever read. I was tearing through the pages to eagerly find the moment when they finally—finally!—meet in real life. An exceptional book from start to finish! 

I absolutely adored the way the narrative creates almost continual laugh-out-loud moments whilst tackling some pretty heavy themes.

Drug abuse and its effect on others is handled in a genuinely uplifting way, alongside hilarious family and relationship dynamics. I love Keyes’ ability to shine light through darkness every time.

The title says it all—Paris is always a good idea! My now-husband romantically invited me to meet him in Paris, way back when, so it’s a special place for me. So is this book, which is a fun, emotional story about love, wanderlust, and finding one’s self.

Chelsea Martin threw herself into work to cope with her mother’s death. Seven years later, her father announces he’ll remarry, prompting Chelsea to examine her own life. She plans a trip to Europe to retrace the last time she remembers being happy.

I adore Chelsea for her bravery and this book for transporting me to gorgeous places, from Paris to Ireland and a vineyard in Italy. 

I love Eve Fletcher, who hates to be called Mrs. Fletcher, particularly now that she is divorced from Mr. Fletcher and her only son Brandan is off to college.

This story about a woman in mid-life reigniting her own sexuality and reinventing herself is at times hilarious, disturbing, raunchy, melancholy, deeply sad, and very sweet. There’s a lot of porn, which is equal parts silly, sexy, and strange. Another great character is Margo, a trans woman who teaches Eve’s Gender Studies class at the local community college.

I read this book in two days while routing for all the brave and imperfect characters as they struggle with their physical and emotional needs.

I loved the voice of Tiffany, the murderous head sorority girl of this novel, so much so that I was very willing to overlook the fact that she was a serial killer. (We all contain multitudes, right?!) Like My Sister, the Serial Killer, this book manages to be tense, dark, and funny all at once, which truly ticks so many of my reader boxes.

This book is also set in Los Angeles, where I live, and I guffawed at its satiric portrayal of a certain type of Angeleno: perma-blonde pumped full of glamorous toxins and is willing to take anyone down a notch if it means “manifesting her highest self.” I thought this book was a truly dark, murderous blast.