The Many Loves of Dobie Gillis

1959 - 1963

This quirky teen comedy follows the day-to-day trials and tribulations of Dobie Gillis, a high school student whose only ambition in life is to get a girlfriend (any girlfriend at all). Based on book series by Max Shulman.

Stars: Dwayne Hickman, Bob Denver, Frank Faylen, Florida Friebus, Sheila James Kuehl, Steve Franken, Tuesday Weld
Created by: Max Shulman
Tags: adaptation, family, teens, quirky

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Episode Tropes

Season 1

Tonsillectomy: Episode 6, "The Sweet Singer of Central High" (1959). Dobie gets his tonsils removed, and the "scar tissue" makes him a really good singer temporarily.
Cyrano de Bergerac: Episode 7, "Greater Love Hath No Man" (1959). Dobie offers to help Maynard get a girl to like him by acting as his Cyrano and telling him what to say to her.
Romeo and Juliet: Episode 9, "Dobie Gillis, Boy Actor" (1959). Dobie tries out for the school play to impress a girl.
Sixteen Candles: Episode 11, "Dobie's Birthday Party" (1959). Dobie's parents pretend they forgot his birthday so he won't know they're planning a surprise party. He gets pissed and refuses to go home, missing the party completely.
The Old Inflatable Raft Gag: Episode 12, "Deck the Halls" (1959). Maynard buys a raft from the Army surplus store for his dad for Christmas, and he asks Mr. Gillis to keep it at the store to hide it, but he forgets to tell him not to pull the cord that inflates it.
The Star Boarder: Episode 14, "The Gaucho" (1960). The Gillises need extra cash, so they decide to rent out Davey's room while he's away at college.
Election: Episode 15, "The Smoke-Filled Room" (1960). Thalia convinces Dobie to run for junior class president against Milton Armitage in the hopes he'll have a future in politics and make lots and lots of money.
Top Fist: Episode 16, "The Fist Fighter" (1960). To impress Thalia, Dobie gets the toughest guy in town to pretend Dobie kicked his ass. Rumors spread about Dobie's fighting prowess, leading to his earning the nickname "Top Fist."
Hey, Kids, Let's Put on a Show!: Episode 26, "That's Show Biz" (1960). The PTA puts on an annual talent show, and Dobie talks Mr. and Mrs. Gillis into joining in order to impress his new girlfriend's parents.
Murphy Bed: Episode 28, "Live Alone and Like It" (1960). Dobie and Maynard move in together, and their new apartment has a Murphy bed.
The Odd Couple: Episode 28, "Live Alone and Like It" (1960). Dobie wants to be independent, so he moves out of his parents' house and rents an apartment with Maynard.
Family Reunion from Hell: Episode 29, "The Big Sandwich" (1960). Mr. and Mrs. Gillis spend a miserable weekend at a family reunion with a bunch of jerks.
Where There's a Will: Episode 31, "Where There's a Will" (1960). Mr. Gillis's lawyer tries to convince him to make out a will, but he's afraid that if he does, he'll die.
Seen the Doctor: Episode 35, "The Unregistered Nurse" (1960). Dobie falls in love with a nurse, but she's not interested in him, so Dobie decides to play on her sympathy to win her over. He looks up an illness that he thinks he can convincingly emulate and goes to the doctor's office, but the disease turns out to be much more serious than he thought.

Season 2

Take Good Care of My Baby: Episode 3, "Take Good Care of My Baby" (1960). Maynard finds an abandoned baby in the park.
Trading Places: Episode 4, "Dobie Goes Beatnik" (1960). Dobie and Maynard pose as each other to impress the head of the Bisons for Mr. Gillis.
Suddenly Psychic: Episode 5, "The Mystic Powers of Maynard G. Krebs" (1960). Maynard suddenly has psychic powers and is asked to predict the winner of the presidential election. At the end of the episode, he loses his powers as suddenly as he gained them.
Gruesome Gift: Episode 6, "The Face That Stopped the Clock" (1960). Dobie buys an ugly clock from the store where Maynard works to make him look good to his boss.
Found Money: Episode 7, "Maynard G. Krebs, Boy Millionaire" (1960). Maynard finds a purse full of money and turns it in, but it's not claimed, so he gets to keep it and spends it on a big party.
A Christmas Carol: Episode 10, "Jangle Bells" (1960). Maynard and Chatsworth are both throwing Christmas Eve parties, and Zelda tries to convince Dobie to attend Chatsworth's party instead of Maynard's to improve his social standing. As Dobie struggles with his decision, he has a Christmas Carol style dream where he's visited by the ghosts of Christmas past and future, who show him that Maynard's friendship is more important than social climbing.
Monkeying Around: Episode 27, "Spaceville" (1961). The Army selects Dobie to join a chimpanzee named Corporal Killroy in a space travel experiment that requires them to live in a simulated space capsule for 30 days.

Season 3

See You in Court: Episode 3, "Move Over, Perry Mason" (1961). When Maynard injures his wrist in a gumball machine at the Gillis family grocery store, his law professor encourages him to sue and represents him in court.
American Gigolo: Episode 5, "The Gigolo" (1961). Maynard starts making money serving as an escort for college girls whose boyfriends are away at other schools.
Election: Episode 13, "Blue-Tail Fly" (1962). Dobie decides to run for student council to impress a girl. His opponent is Chatsworth, who uses old protest songs to boost his popularity.
Election: Episode 14, "I Do Not Choose to Run" (1962). Mr. Gillis decides to run for planning commissioner, and a key campaign issue causes Dobie to support his opponent instead of him.
Playing the Market: Episode 20, "The Big Blunder and Egg Man" (1962). Dobie decides to invest in the stock market to impress a business-minded girl. At first he cleans up, but when he doesn't sell at the right time, he loses everything.
Big Brothers Big Sisters: Episode 22, "Like Oh, Brother" (1962). Dobie and Maynard volunteer to be big brothers at a home for disadvantaged boys.

Season 4

Hostage Situation: Episode 17, "All Right, Dobie, Drop the Gun" (1963). An escaped convict and his girlfriend hold the Gillis family hostage while they hole up at the grocery store, and Maynard is their only hope for rescue.
Handcuffed Together: Episode 21, "The Beast with Twenty Fingers" (1963). Maynard and Mr. Gillis get their pinkies locked together in a Gypsy "love link" they can't unlock, and Mr. Gillis is about to attend a grocers convention.
Monkeying Around: Episode 25, "The Little Chimp that Couldn't" (1963). The dean of the junior college wants to transfer an underperforming chimpanzee named Seymour from Dobie and Maynard's psychology class to the medical research wing, but he gives Maynard one week to teach Seymour some useful skills to justify keeping him in the class.
Vacation from Hell: Episode 27, "The General Cried at Dawn" (1963). When Dobie and Maynard vacation in the fictional country of Boca Dolce, the local rebels notice Dobie bears a strong resemblance to a tyrannical general, and they abduct both of them and force Dobie to impersonate him.
Raging Bull*&@!: Episode 31, "Requiem for an Underweight Heavyweight" (1963). When Maynard accidentally swallows some experimental energy pills that give him superhuman strength, Mr. Gillis decides to make some money by making Maynard a boxer.
Rigged Raffle: Episode 36, "The Devil and Dobie Gillis" (1963). Chatsworth wants Dobie to help him rig the raffle at his family's charity bazaar so they can split the $5,000 prize.

Character Tropes

Hopeless Romantic: Dobie Gillis - Played by Dwayne Hickman.
Idiot Savant: Maynard G. Krebs - Played by Bob Denver.
Mild Mannered Man-child: Maynard G. Krebs - Played by Bob Denver.
Rich Snob: Milton Armitage - Played by Warren Beatty.
Rich Snob: Chattsworth Osborne, Jr. - Played by Steve Franken.
Frenemy: Chattsworth Osborne, Jr. - Played by Steve Franken.
Gold Digger: Thalia Menninger - Played by Tuesday Weld.
The Gaucho: Carlos Romero - Played by Joe Sonessa in season 1, episode 14, "The Gaucho" (1960).