The most prized possessions are literal prizes, and the kinds of prizes that someone goes after can say a lot about them. Whether it's something they want now, or something they've owned for years it can serve as shorthand for the character's motives and desires.
The fact that the character put actual effort into trying to secure this object gives it far more weight than something they might have just bought or picked up by chance. If they won it from someone else, it can even serve as shorthand for a conflict between them and the person who lost it (although never the actual cause, as is the case with an Apple of Discord).
Often the "backstory" to a character's Iconic Item or #1 Dime in works that aren't trying to be especially serious about it (although it doesn't have to be either of those; it could easily be worthless to the character now). In these cases you can expect the character to have gone to a lot of effort to secure their prize (e.g. sending multiple entries to a sweepstakes, or putting a lot of effort into winning a clearly rigged fairground game). Compare/contrast Friend-or-Idol Decision, where the fact that a person (usually) gives up something that he's been looking for a long time says something about him.
- The leg lamp in A Christmas Story is a "major award" that Ralphie's dad wins in a contest and proudly displays in the window. It's a ridiculous lamp, but he prizes it simply because he won it. Also, the Orphan Annie decoder that Ralphie drinks so much Ovaltine for turns out to be nothing but an advertising gimmick, leaving him disillusioned.
- In Despicable Me, one of the turning points in Gru's fondness towards the girls happens when he takes them to an amusement park and the owner of a shooting booth holds back on giving Agnes the stuffed unicorn she won on a technicality. Gru pays for another turn for himself and uses his own gun, demolishing the booth and convincing the owner to give Agnes the unicorn. Gru winning the unicorn for Agnes is significant because before, he was just trying to use the girls for his plan and get them out of his life again as soon as possible.
- In Children of the Lens Kimball Kinnison wins ten millos in a side bet with his son. He has the one-cento coin mounted in a thousand-credit frame and presented to the librarians who won the bet for him.
- In one Calvin and Hobbes storyline, Calvin eats multiple boxes of Chocolate-Frosted Sugar Bombs so he can send away for a beanie hat. He then waits for what seems (at least to him) like forever and suffers through trying to assemble it (and the trauma of thinking he broke it), because, being an imaginative kid, he thinks the beanie will enable him to fly. When it doesn't, it comes as a major disappointment.
- The fourth season of RWBY reveals that the hoody Jaune's been wearing under his armour since he was introduced is a promotional item he won by sending in hundreds of "Pumpkin Pete" cereal box tops. As a bonus it ties into the fact that his armour now incorporates elements and metal from Pyrrha's, since she was the spokesman for the brand.
- In Gravity Falls, Mabel has great love for her pig Waddles which she won at a carnival in "The Time Traveler's Pig". She is greatly upset when, in an alternate timeline, her rival Pacifica Northwest wins the pig instead.
- Steven Universe: In "Too Short to Ride" Peridot spends much of the episode trying to win an alien doll from a carnival game. The obvious Little Green Man joke aside, she spells out why she wants it by gushing over both its large head (swollen with thoughts!) and "compassionate eyes" ("It understands!").
- My Little Pony: Friendship Is Magic: According to a promotional video, Applejack won her trademark Stetson hat in an apple-bobbing contest.