10) A Piece of the Action
One of Trek’s more goofy episodes—the Enterprise visits a planet that hasn’t technologically evolved beyond early 20th century technology, which is basically an excuse for them to visit 1920s New York without actually doing a time travel episode—“A Piece of the Action” makes up for its silly glee (and the clear relish Shatner and company have for riffing off the classic gangster story aesthetic) by having Kirk just run circles around his adversaries with some grade-A bullshitting. The scene where he creates card game Fizzbin completely out of thin air to trick his captors into freeing himself, Spock, and Doctor McCoy is just delightful.
