Tippy Teen #23

Tippy Teen and Tommy Trippit are back with a collection of corny jokes and wisecracks that'll make you groan—from a tiny watchdog to why milk stays fresh in the cow, this vaudeville duo trades one-liners like a well-oiled comedy machine. It's pure joke-book humor, the kind of groan-worthy gags that defined teen comedy in 1969.

Egghead falls hard for Brains Baxter, Centerville's brilliant new girl—a sharp-minded genius who speaks fluently about quantum theory and atomic energy. When he invites her over for an intellectual evening, their wires get hilariously crossed as she persistently misinterprets his attempts at brainy conversation as romantic advances, leaving our befuddled hero scrambling to keep things on a purely mental level.

When Tippy and her friends show up to school sporting the latest trend—colorful buttons with slogans and witty slogans—Miss Snodgrass is appalled by what she sees as childish nonsense. As the teacher's disapproval grows, she decides it's time to involve Principal Phogg and put a stop to the button craze once and for all.

Tippy sets her sights on becoming a cheerleader to get closer to Tommy, the football team captain—but her enthusiastic tryouts end in a spectacular accident that lands her with a broken leg. Stranded in the stands during the big game, Tippy's determined spirit somehow becomes the spark that ignites her team's comeback, turning her mishap into an unexpected win.

When Peggy hatches a scheme to break up Tommy and Tippy by setting the lovesick Horace Acknee up with Tippy, she doesn't count on the plan backfiring spectacularly—leaving everyone tangled up in a romantic mess of their own making. This 1969 romp proves that in the teenage dating game, the best-laid schemes have a way of catching the schemer off guard.

Tippy's got a list of life's most frustrating ironies—from the moment your dad finally has nothing to say to your date, to acing homework the one day you didn't study, to Murphy's Law striking the instant you borrow the family car. This two-page humor piece is pure teen comedy, a rapid-fire collection of "why is it?" moments that'll have you nodding in recognition—right up until the final punchline about those expensive dancing lessons.

When a cocky swimmer named Tommy trash-talks his way into a big race against the arrogant Ashley Hartburn, his brainy friend Egghead volunteers to be his trainer—only to reveal, the morning of the competition, that he can't actually swim. In a desperate move, the gang hatches a scheme involving one of Egghead's inventions to level the playing field, but things take an unexpected turn when the gadget goes missing right at the starting line. What unfolds is a hilarious clash of ego, ingenuity, and sheer willpower that proves sometimes the real victory lies in discovering what you're truly capable of.