SpongeBob wakes up, stubs his toe, and starts crying. He rips his favorite shirt and starts crying again. He goes downstairs and hears a sad song on the radio; he cries again.
At work, he flips a Krabby Patty, which lands on the ground when Mr. Krabs startles him. SpongeBob then cries once again. Squidward gets irritated of SpongeBob's crying and he yells at him. SpongeBob then cries, wailing, "You yelled at me!"
Squidward tells SpongeBob that he cries too much; SpongeBob denies it. Squidward then pulls up a TV and plays a video of a trillion tears and millions of places where SpongeBob has cried over those years. He then makes a bet with SpongeBob that he couldn't last until midnight without crying.
After the bet is made, Squidward follows SpongeBob home to make sure he cries, and tries to make SpongeBob cry over things like a beautiful sunset, sad news stories, sad news stories with funerals, a sad song on the clarinet, and a sad bedtime story.
Amazingly, SpongeBob manages to hold in his tears until midnight, despite all of Squidward's best attempts, and after midnight, SpongeBob cries all over Bikini Bottom like crazy. Squidward comes over for a slumber party the next night, and the episode ends with Squidward crying and screaming and SpongeBob comforting him.
( ‣ ) Associated production music
( • ) Original music
( ◦ ) SpongeBob music
• ? - Sage Guyton, Jeremy Wakefield [title card] • ? - Sage Guyton, Jeremy Wakefield [SpongeBob wakes up] ‣Hawaiian Cocktail - Richard Myhill [SpongeBob cries] • ? - Sage Guyton, Jeremy Wakefield [SpongeBob goes into his closet] ‣ ? [sad song] • ? - Jeremy Wakefield ["That SpongeBob is such a crybaby."] • ? - Michael Bolger, Nicolas Carr ["SpongeBob, guess what!"] ‣ ? ["He was a good little Krabby Patty."] ‣Drama Link (e) - Hubert Clifford [Squidward annoyed by SpongeBob's crying] ‣Drama Sting - Sage Guyton, Jeremy Wakefield ["SpongeBob, will you stop crying?!"] • ? - Jeremy Wakefield ["You yelled at me!"] ‣ ? ["All right, look."] ‣South Pacific Island II - Victor Cavini [montage of SpongeBob crying] • ? - Nicolas Carr [thousands of tears later...] ‣South Pacific Island II - Victor Cavini ["Wow, guess I do cry a lot."] • ? - Nicolas Carr ["Excuse me a minute."] ‣Seaweed - Steve Belfer [SpongeBob calls Patrick] ‣Cartoon Sting 1 - Gerhard Narholz, Nicolas Carr, Barry Anthony [SpongeBob makes a bet with Squidward] ‣Drama Link (c) - Hubert Clifford [Squidward laughs] ‣Hawaiian Flower - Jon Jelmer [sunset] •Steel Sting - Jeremy Wakefield ["Oh, well, sunset's over."] ‣O Makalapua B - Kapono Beamer [Gary sleeping] ‣ ? [mail arrives] ‣Maui Beach - Hans Haider [postcard from SpongeBob's parents] ‣Tympup B - Sammy Burdson, John Charles Fiddy ["No problem."] •Hawaiian Sting - Nicolas Carr ["No problem."] •Bikini Bottom News Theme - Nicolas Carr [news on TV] ‣International Law - Peter Yorke [snail caught in tree] •Bikini Bottom News Theme - Nicolas Carr ["Coming up: an interview with a manatee..."] ‣Drama Link (o) - Hubert Clifford ["Sad news for Mermaid Man and Barnacle Boy fans."] ‣Alpine Holiday - Harry Bluestone [Squidward changes the channel] ‣Drama Link (f) - Hubert Clifford [SpongeBob throws the TV out the window] • ? - Jeremy Wakefield ["I'm gonna watch it all night!"] ‣ ? ["It's getting late."] ‣ ? ["What would you say to a little music?"] • ? - Nicolas Carr, Barry Anthony [Squidward playing clarinet] ‣Drama Sting - Sage Guyton, Jeremy Wakefield [Squidward gets angry] ‣ ? ["Time really does fly when you're having fun!"] ‣Befuddled Gent - Phillip Green [bedtime story] ‣Danger Sign - Harry Bluestone, Emil Cadkin [SpongeBob trying not to cry] ‣Frightmare - Jane Antonia Cornish [it's almost midnight] • ? - Jeremy Wakefield [Squidward sighs] •Chase Cue 2 - Sage Guyton, Jeremy Wakefield [SpongeBob bursts out crying] ‣Friends and Family - Phillip Green, Geoff Love, Ken Thorne [ending]
SpongeBob can be seen shedding a tear during the news story about the snail, which means Squidward won the bet all along.
However, when he said that not one tear could’ve been shed, he might have meant SpongeBob could not cry out loud.
Squidward's line "I just threw up in my mouth a little," is a reference to the movie Dodgeball: A True Underdog Story.
On the radio, if one would listen carefully, the announcer said the song was by Eely Dan. This is an obvious reference to the jazz rock band Steely Dan. Also the next song was by Lionel Fishy. This is also a reference to Lionel Richie.
The radio announcer also states that the song's name before "Sad Songs" was Aja, a song by Steely Dan on the album of the same name and a song called "Sad Song" by Paul Williams.
The name of this episode is possibly a reference to Enya's album, "A Day Without Rain".
In the subtitles on TV, SpongeBob says "Stop. It burns," when he would normally say "Sob. Whimper."