“The negative just makes for a better story: the plane was delayed, an infection set in, outlaws arrived and reduced the schoolhouse to ashes. Happiness is harder to put into words.” David Sedaris has never been afraid of making dark jokes and his latest collection of short stories, “Calypso,” is no exception to this trend. Although Sedaris is known for this type of humor, the collection’s focus on his family—particularly his deceased mother and sister as well as his aging father—makes these tough jokes hard to stomach at times. Amid the darkness is the same wit that Sedaris always brings to his stories and although the difficult subjects are hard to read with this humor interlaced throughout, “Calypso” is perhaps Sedaris’ most raw collection.

Sedaris is gifted with a wit that can take some of life’s most pressing questions and turn them into a gut-busting joke. He ponders why Christians feel the need to portray Jesus as perfectly handsome. “What would happen, I often wonder, if someone sculpted a morbidly obese Jesus with titties and acne scars, and hair on his back?” And while to some degree he is making fun of the practice, he’s also hinting at a larger point. “Doing good deeds doesn’t make you good-looking.” Sedaris wraps these important societal questions in hilarious quips and dirty jokes, but the weight of them remains nonetheless.

What makes “Calypso” different from Sedaris’ other collections are the themes he has chosen to focus on, mainly his family. He uses his beach house in Emerald Isle, named Sea Section, as a home base since during his childhood Sedaris’ family would annually rent a condo in Emerald Isle and as adults the remaining members congregate at the Sea Section. Many of his stories begin and end here, but veer off on tangents about childhood Emerald Isle trips or memories of family.

Family is no easy task to write about, especially for Sedaris. “Now We Are Five,” the second story in the collection, begins: “In late May 2013, a few weeks shy of her fiftieth birthday, my youngest sister, Tiffany, committed suicide.” Yet the story departs from this somber tone at times, discussing the purchase of the Emerald Isle beach house and the reinstatement of family vacations to the beach. Other stories, such as “Why Aren’t You Laughing?” and “The Comey Memo,” explain his complicated relationships with his parents. Sedaris discusses how much he and his siblings doted on their mother, yet no one addressed her alcoholism. He recounts arguments with his aging father that are hilarious, but also upsetting as Sedaris tries so hard to connect when the two have very little in common. Sedaris family stories are almost always funny, but the humor seems to come at a price.

Underneath the humor is heartbreak, such as when Sedaris ponders about his sister’s death, “Doesn’t the blood of every suicide splash back in our faces?” It is lines like these that stray from his usual and may be too much to bear for Sedaris’ usual reader looking for a good laugh. These emotional moments add depth to his writing. This collection is a departure from Sedaris’ norm due to this newfound darkness, which is surprising for an author who is known for his particularly dark humor.

This is Sedaris’ most personal collection of stories, which sometimes make it difficult to handle his darker jokes. However, it provides more information about the author than ever before. Sure, his past writings have told of his various travel stories or crazy neighbors in the many cities he has lived in. “Theft By Finding” was years worth of journal entries, describing the times spent making ends meet and getting drunk or high whenever possible. But “Calypso” explores personal family dynamics that have only been briefly mentioned in the past, making this collection more tender and more painful than his others.

—Staff writer Caroline E. Tew can be reached at caroline.tew@thecrimson.com. Follow her on Twitter @caroline_tew