As the Class Clown with a stuttering disorder, she's nicknamed "Jacky Ha-Ha". The assistant principal suggests Jacky participate in the school play instead of serving detention as long as she doesn't get any new punishments, meaning she has to find a way to behave better.
The book has received two sequels—Jacky Ha-Ha: My Life is a Joke and Jacky Ha-Ha Gets the Last Laugh—and a graphic novel adaptation of the first two books.
Jacky Ha-Ha contains examples of:
- Alliterative Name: Jacky's younger sister Hannah Hart.
- Annoying Younger Sibling: Emma to all her sisters. Jacky manages to be both this trope and an Annoying Older Sibling in equal measure as her antics don't often endear her to her older siblings and some of them end up making trouble for Riley.
- Big Brother Instinct: Jacky's is mostly demonstrated in her relationship with Meredith; a surefire way to piss off Jacky is to make fun of Meredith, especially if you're making racist remarks.
- Caught on Tape: Audio version; Jacky, in disguise, records Ringworm and his cousin Trevor confessing to stealing from the stalls on the boardwalk and several tourists on a cassette tape.
- Class Clown: Jacky frequently makes jokes and pulls pranks, partially earning her the nickname "Jacky Ha-Ha".
- Cool Aunt: Mrs. O'Mara to Schuyler during book 2; he thinks the world of her and she's the only person who saw him as a grieving and worried son with a father fighting in Kuwait instead of a no good Delinquent.
- Cool Teacher: Mrs. O'Mara is Jacky's equal in wit, and inspires her students well.
- Dad's Off Fighting in the War: Jacky's mom is in Saudi Arabia during Operation Desert Shield until the end of the first book.
- Schuyler's dad is mentioned to be off in Kuwait during Book 2, which caused him to act out before Mrs. O'Mara took custody of him.
- Fair Cop: Jenny Cornwall, ex-cop and "prettiest girl on the beach".
- Ferris Wheel of Doom: Jacky makes frequent night trips climbing on the local Ferris wheel to its top. For an adult, this is very dangerous for a child to do, so how her parents respond when they catch her one night is expected and realistic.
- Flowery Insults: Schuyler spouts a bunch of them taken from Shakespeare himself; Jacky is fascinated.
- Food Fight: Jacky, Bill, Meredith, and Jeff start one in McDonalds, getting them kicked out.
- Lethal Chef: Mrs. O'Mara; her pancakes are so bad Schuyler considers eating them to be fair punishment for Jacky getting him wrongfully accused of theft.
- Massive Numbered Siblings: The Hart family has seven daughters: Sydney, Sophia, Victoria, Hannah, Jacky, Riley, and Emma.
- Middle Child Syndrome: Being a middle child is part of the reason Jacky constantly seeks attention.
- Mistaken for Cheating:
- Jacky thinks her father is having an affair with Jenny Cornwall and accuses him outright. She's actually helping him study to become a cop.
- In the second book, Jeff, seeing Victoria, lets Schuyler, seeing Sophia, try on his Bossy the cow costume and Schuyler gets stuck. While they're trying to get him out, Victoria runs up to who she thinks is Jeff and starts gushing about how in love with him she is. Jeff is rather heartbroken and when Sophia shows up just as Schuyler gets the cow head off, both girls are furious at both him and each other. It falls on Jacky to set things right with a Zany Scheme because no one is willing to listen.
- Mistaken for Suicidal: When Jacky is found after climbing on top of a Ferris wheel, Hannah thinks she's about to jump off.
- Mistaken for Thief: Late in Book 2, Jacky and several of her fellow young actors go into a store, forgetting they're in full costume; they have to reassure the clerk they're not going to rob him.
- Nostalgia Filter: Jacky pointedly averts this, noting how parents often embellish what happened in their childhoods, makes no bones about how hers had the least glorious and funny periods of her life, and pokes fun at how people used to have mullets and dance the Macarena.
- Sad Clown: Part of the reason Jacky makes jokes and acts out is to distract herself from her mom serving in Saudi Arabia and her dad barely ever being home.
- Small Name, Big Ego: Travis Wormowitz in book 2, who makes racist remarks about Meredith and generally acts as if he's the only competent person in the cast, mocking the idea of understudies (despite it being standard theater protocol) and framing Schuyler for theft because Mrs. O'Mara, Schuyler's aunt, got him kicked out of the Midsummer's Night Dream production.
- Speech Impediment: Jacky has a tendency to stutter, and she hates when it's referred to as a speech impediment.
- Step Servant: Downplayed. While her parents largely weren't around, Jacky and most of her sisters did the housework. Unfortunately, being the middle child of the family, she was saddled with the most degrading tasks (i.e. cleaning the bathroom).
- "Where Are They Now?" Epilogue: All the books have these, since they're each being told as a Whole Episode Flashback by adult Jacky—with Jacky detailing what happened to characters relevant to each book's story line, e.g. like how her dad passed his cop test or that Sophia and Victoria both married the guys they were dating during book 2. This also extends to her, since she married Bill, the boy she had a crush on in the first book, and has two daughters.
- Whole Episode Flashback: Each book is told by a now-adult Jacky telling stories of her childhood; in the first two books, it's to her two daughters.
- Zany Scheme: Jacky is prone to these; sometimes they work, like using her paycheck to stage an ice cream event to repair the damaged relationships for Jeff/Victoria and Sophia/Schuyler, and sometimes they don't, like using a band performance to accuse a pair of thieves.
