Felix finds himself unable to sleep for days on end, driving him and Oscar to the brink of madness.
This episode includes examples of the following tropes:
- Caretaker Reversal: A lot of the plot has Oscar trying to help Felix overcome his insomnia. At the end, Felix is happily slumbering, but Oscar can't fall asleep.
- Chekhov's Gun: When Oscar asks Felix if anything's bothering him at work, Felix mentions a recent ad campaign for watches that went very well. It turns out the client gave Felix a new (electronic) watch, and Felix has unconsciously been missing the sound of his old watch ticking as he goes to sleep.
- Crazy Jealous Guy: Partway through the episode, Oscar asks Felix if anything went wrong before he began suffering insomnia that might be keeping him awake. The event they fix on is Felix seeing Gloria in the supermarket with another man. However, even after it is resolved, Felix can't fall asleep.
- Exhaustion-Induced Idiocy: In his sleep-deprived state, Felix does things like give Oscar two knives for eating breakfast, and drink orange juice with cream and sugar.
- Formally-Named Pet: The toy variant appears with Felix's old teddy bear, "Mr. Friend."
- Hope Spot: Midway through the episode, Oscar finds out that Felix saw his ex-wife with another man and the two suspect that may be causing Felix's insomnia. Felix puts Murray on the case, and Murray finds out that the man simply got into a fender bender with Gloria and they were discussing a settlement. However, that night Felix comes into Oscar's room, as wide awake as ever.
- Insomnia Episode: As implied by the title, most of the plot covers Felix being unable to sleep. Oscar tries all manner of things, from analyzing what might have upset his roommate to buying him a water bed, in an attempt to get Felix to sleep. However, everything fails until the end of the episode.
- Manchild: Felix gushes over his childhood toys and books that Oscar dug out of storage, begs to be allowed to stay up a little longer, and happily listens to Oscar reading a series of children's tales.
- Shout-Out: When Murray comes into the apartment in "plainclothes" garb, he asks if he looks like Columbo.
