The Enterprise heads to the Omega Sagitta system, where a pair of twin planets are living under a precarious peace treaty with each other. They unexpectedly encounter a broken down cargo ship with a single person on board. That person is the irreverent Captain Okona (Billy Campbell). Picard offers to beam Okona aboard while a maintenance crew repairs his ship.

Okona lays the charm on thick with the crew, especially the ladies, causing Data to grapple with the fact that he doesn't find Okona's jokes, or any humor in general, to be funny. Data seeks Guinan for guidance, and she recommends that he study up with a computer. He enlists the holodeck for guidance, calling up a hologram of "the greatest comedian ever," a 23rd century comic played by Joe Piscopo. Data tries out some routines he's learned from the comic, but Guinan still isn't laughing.

Meanwhile, the Enterprise encounters a ship from planet Atlec, which prepares to fire on them with lasers. Picard finds their weapons so laughable he actually drops the main shields just to mock them, at which point the captain of the vessel demands he turn over Okona for knocking up his daughter. A second ship, this one from planet Straleb, appears, also demanding Okona be handed over for stealing a valuable jewel. Picard realizes that whichever captain he gives Okona, the other will start a war over it.

Picard opts to finish repairing Okona's ship and let him fend for himself, but Okona instead invites both ship captains to the Enterprise to sort things out. The whole incident turns out to be a silly misunderstanding – the son of the Straleb captain had impregnated the daughter of the Atlec captain and asked Okona to give her the jewel as a marriage offering. Everyone makes up and has a good laugh... even Data, who finally manages to accidentally tell a proper joke.

This episode provides examples of:

• Actor Allusion: Of everyone on board, Data seeks out Guinan for guidance on having a sense of humor, which makes sense considering that Whoopi Goldberg is a noted comedian.
• Ambiguously Human: It's never made clear if the locals are humans or Human Aliens.
• Artistic License – Physics: Invoked when Okona indirectly mentions the old urban legend about someone carrying a truck filled with birds and managing to keep it at the right weight by making sure at least half of the birds are always flying. Data begins to explain why that wouldn't actually work in reality, but Okona says he was joking and chides Data for being so literal-minded.
• The Cameo: Joe Piscopo was a pretty hot comedian in the late 1980s, so his appearing in a small role was a big deal.
• Cannot Tell a Joke: Data finds himself unable to find things funny, or to tell a joke and have somebody laugh, spurring his subplot in the episode.
• The Comically Serious: When Data is told his timing ruins his attempts at humor, he replies with "My timing is digital." Then he can't understand why Guinan finds that one funny.
• Deadpan Snarker: Picard and Riker get in a good quip dialogue when one of the two faction vessels locks targeting to fire outdated laser weaponry onto the Enterprise:
  Lt. Worf: [in disbelief] Captain, they are now locking lasers on us.
  Cmdr. Riker: Lasers?!
  Worf: Yes, sir.
  Capt. Picard: Lasers can't even penetrate our navigation shields. Don't they know that?
  Riker: [in equal disbelief] Regulations... do call for yellow alert.
  Picard: Mmm. Very old regulation. Well, make it so, Number One. [to Data at Conn] And... reduce speed. Drop main shields as well.
  Riker: May I ask why, sir?
  Picard: [with joking deadpan sarcasm] In case we decide to surrender to them, Number One.
• Expy: Okona is a pretty clear attempt to insert a Han Solo-like character into the Star Trek universe.
• "Everybody Laughs" Ending: Averted, despite Data's best efforts. The episode ends on Data trying to make everyone else laugh (saying, "Take my Worf - please!"), but nobody does.
• Fashionable Asymmetry: Okona's outfit has elements of assymetry, particularly on his pants.
• Handshake Refusal: Picard returns Okona's outstretched hand with a Death Glare because of the diplomatic situation he's involved in.
• Handsome Lech: Combined with Chivalrous Pervert. Okona manages to work his way through a surprisingly large number of the Enterprise's female crew during his brief stay, starting with successfully hitting on the transporter operator (a pre-stardom Teri Hatcher, no less) seconds after arriving.
• Informed Attribute:
  • Okona is said to be "mischievous, irreverent, and somewhat brazen." A lot of his actions support this description. He spends most of his screen time making jokes and hitting on ladies. He almost comes to blows with Worf after refusing to leave a lady's bedroom to answer Picard's summons. In the end, it's revealed that he's been playing secret matchmaker for a pair of star-crossed lovers. However, the episode receives a lot of criticism for Okona not being as "outrageous" as the script seems to think he is.
  • Joe Piscopo's character's status as a comedian worthy of inclusion in the Holodeck's hall of comics, given how utterly unfunny every single thing he says or does is during the entire episode.
• Jerk with a Heart of Gold: Okana may be somewhat irresponsible and cavalier, but he does play matchmaker between the two Star-Crossed Lovers.
• Lovable Rogue: Okona is treated this way by everyone in-universe. The audience doesn't get to see him do anything or hear any stories to confirm it though.
• Mistaken for Name: Okona does this as a joke — Wesley introduces himself as "Wesley. Wesley Crusher", so Okona calls him "Wesley-Wesley Crusher".
• No Challenge Equals No Satisfaction: The "Data tries to learn about humor" subplot ends with him performing in front of a holodeck audience that laughs at his jokes no matter how bad they are. He then realizes that he's wasting his time and shuts down the program.
• No-Sell: It's made pretty clear that laser fire from the Altec and Straleb ships would have no effect on even the weakest Deflector Shields protecting the Enterprise.
• Orphaned Setup: Data asks the comic to tell a joke. He then has the computer increase the speed at which the program is talking, to the point that the punchline is lost.
• Papa Wolf: Debin is outraged by Okona supposedly impregnating his daughter, Yanar, and leaving her and her unborn child behind. He’s chased after Okona in hopes of restoring his daughter’s honor by making him marry her.
• Really Gets Around: Worf notes that Okona has recently visited three crewmembers' quarters.
• Secret Relationship: Between Benzen and Yanar. They both kept their relationship a secret because they feared what could happen if they told their fathers, like going to war with the other planet or being disowned.
• Shout-Out:
  • Data does a Groucho Marx impression when trying to do comedy.
  • Data practices some Jerry Lewis slapstick in the holodeck.
  • The "Say goodbye, Data.” “Goodbye, Data." exchange is a shout-out to Rowan and Martin's Laugh-In, and a invokedBeam Me Up, Scotty! for The Burns and Allen Show.
• Small Name, Big Ego: The representatives from Altec and Straleb don't seem to realize what small fries they are in the galactic scheme of things. They make demands and threaten Picard with antiquated technology, little realizing that they're "glob flies," as Worf terms them.
• Yank the Dog's Chain: Performing to raucous laughs in the holodeck, Data believes he has finally figured out comedy, but then he gets the same reaction to simply returning a thumbs up to Piscopo's character. Data begins to realize that the audience is programmed to laugh at everything he says and does. After testing that a few times, he deactivates the audience and the comic.