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. Squidward tells SpongeBob that he cries too much, SpongeBob denys it. Squidward then pulls up a TV and plays a video of a trillion tears and millions of places SpongeBob where 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, 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 SpongeBob comforting him.
The title card is identical to Pickles, but it's a bit zoomed-in more.
The rules of the no crying contest are, if Squidward wins and SpongeBob cries, SpongeBob has to wash his bike, clean out his rain gutters, and do all of Squidward's tiresome yard work for one year. If SpongeBob doesn't cry, and Squidward loses, he has to attend a sleepover at SpongeBob's house(much to his disgust).
On the radio, if you listen carefully, the announcer said the song was by Eely Dan. This is a 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 songs name before "Sad Songs" was Aja , a song by Steely Dan on the album of the same name.
When Squidward puts the slideshow of SpongeBob crying, none of them were in any episode. Also, he wore his Krusty Krab hat in all of them even though most weren't set at The Krusty Krab.
So Squidward was most likely lying.
The Bikini Bottom Men's Choir made another appearance in this episode.
On the Triton's Revenge DVD, this episode is on the DVD and it includes a deleted scene. It shows, after SpongeBob is "yelled at" by Squidward, Squidward tells SpongeBob "You know there's an old saying, SpongeBob". SpongeBob asks, "What is it?" Squidward answers, "Don't cry over a soiled krabby patty!, and now may I give you a little word of advice... SHUUT UP!!!" SpongeBob starts crying more. Then, it cuts to the chalkboard scene.
When Squidward is making SpongeBob watch TV, it shows a show with a father and his son. The house shown looks like SpongeBob's Grandma's house. Oddly, SpongeBob doesn't even notice.
Drama Link O - "And finally, sad news for Mermaid Man & Barnicle Boy fans. They will only be showing the Mermaid Man & Barnicle Boy episodes 7 times a day, instead of 8 ..." (then SpongeBob changes the channel)
Drama Link F - SpongeBob throws the TV out the window.