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 titular Captain Okona, whom Counselor Troi describes as mischievous, irreverent, and somewhat brazen. Never mind that he never portrays any of those characteristics throughout the episode, aside from cracking a few jokes and hitting on female crew members. Picard offers to beam Okona aboard while a maintenance crew repairs his ship.
Okona gets to know the crew, and gets frustrated that Data doesnt find his jokes funny. He tells Data that hes missing out on a big part of the human experience, and Data concludes that he is correct, making it his mission in this episode to understand humor. Unfortunately, he chooses as his mentor a holodeck simulation of Joe Piscopo. Predictably, this gets him nowhere.
The Enterprise then 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 gets Okona, the other will start a war over it.
Picard opts to finish repairing Okonas 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 tell a proper joke.
Data: Goodbye, Data.
A shame Data can't stop while he's ahead, though.
This episode provides examples of:
- Ambiguously Human: It's never made clear if the locals are humans or Human Aliens.
- Badbutt: Okona is far from the badass that we're supposed to believe him as.
- Cannot Tell a Joke: Data, spurring his subplot in the episode.
- Casting Gag: Billy Campbell originally auditioned for the role of Riker.
- 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.
- Did Not Think This Through: The natives try to threaten the Enterprise with weapons so relatively primitive it isn't worth the effort of raising shields.
- Everybody Laughs Ending: Averted, despite Data's best efforts.
- 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 seconds after arriving. He has zero charisma or charm that the audience gets to see (though Billy Campbell is a very good-looking man).
- Informed Attribute: The biggest and most consistent criticism of this episode, and it starts in the very title.
- Everything about Okona. Troi's description of him used to top the Informed Attribute page, and Riker's can still be found on the quotes subpage.
- 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.
- 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.
- 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 Such Thing as Alien Pop Culture: Data decides to use the holodeck to ask Ronald B. Moore, a comedian from the 20th century, advice on how to be funny. This is the equivalent of someone in the 21st century asking Thomas Jefferson for comedy tips. Subverted in that, while this is who he ends up with, the computer's initial suggestions are more recent and include other races.
- 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.
- Secret Relationship: Between Benzen and Yanar.
- Series Continuity Error: Data says that he can't get drunk. Sure about that?
- Small Name, Big Ego: After all the build-up about how Okona's a rogue who lives life on the edge, it turns out he's a completely legitimate delivery driver. He gets offended when accused of being a criminal. All the secrecy surrounding his activities is because he takes client confidentiality very seriously.