The Monkees—Davy, Mike, Peter and Micky—are four talented musicians, who open this segment by staging a mock assault on Davy and scaring away Lionel B. Turner, a doctor, during a TV interview. He helps a little old lady across the street and is charged $.15 for his kindness.
The Monkees' manager, Rudy Gunther, a 45 year-old ex-Marine Sergeant who owns a record store, Rudy's Record Rack, sends them to the Riverdale Country Club, where his old Marine buddy Charles Russell is auditioning bands for a Sweet Sixteen Party he is giving his daughter, Vanessa.
When the boys arrive, Mr. Russell and Vanessa are sedately dancing to the square melodies of Sven Helstrom and his Swedish Rhythm Kings. During The Monkees audition—a rocking version of "I Wanna Be Free"—Davy's eyes meet Vanessa's and they fall in love, fantasizing about fun in the Kiddieland amusement park. The Monkees are hired, but Vanessa becomes so involved with Davy that she neglects her schoolwork and flunks history.
At the beach, Jill Gunther, Rudy's 16 year-old daughter and Vanessa's friend, explains to the boys that Vanessa will get a makeup final, but they are in danger of losing a job if she flunks it, too—and that her admirations for Davy is the reason for her failure to concentrate on her schoolwork. Feeling responsible, Davy takes leave of the group to sadly take a stroll down the beach, to a much slower tune of "I Wanna Be Free."
In a fantasy sequence as lawyers in a board meeting, the boys select Davy to help Vanessa pass her final. Having disguised themselves as deliverymen, The Monkees smuggle Vanessa out of the house and improvise a unique history course in which they dramatize historical events in music, resulting in her passing a makeup exam.
However, Mr. Russell still orders The Monkees to be barred from the dance and a guard chases them away, while Sven Helstrom and his Swedish Rhythm Kings perform. When Russell learns The Monkees helped Vanessa pass her history test, he leads a wild but successful chase from the front lawn to the game room to get them back.
When the guard finally corners the boys in the ballroom, Mr. Russell tells him they are invited. The guard bellows, "You've sold out, sir! Your country club, and yourself!!!" and storms off. Mike gets the Swedish Rhythm Kings off the bandstand by announcing that "Norway has just declared war on Sweden, and all the Swedish nationals are to report to their embassy."
The Kings, patriotic beings they are, march off, and The Monkees get the joint jumping with "Let's Dance On." During the number, the partygoers are joined by a drunk from the bar, Dr. Turner and the old lady, and the TV Interviewer, who tries in vain to conduct a "Man-In-The-Ballroom" interview. From the bandstand, Davy sees another girl, and again sparks fly.
Afraid that Davy's new passion may cost them their first job, Micky, Mike and Peter, brandishing balloons as weapons, madly dash after Davy.