Because you like Bill Haverchuck in Freaks and Geeks
The self-proclaimed "only guilty man in Shawshank prison" has wisdom to share, such as the best way to smuggle a Rita Hayworth poster into a Maine prison. See them in The Shawshank Redemption.
Hannah Horvath is kind of a mess, but she owns her messiness in a way few people do. See them in Girls.
Annie Walker can bake a beautiful cupcake, but everything else in her life is a mess. See them in Bridesmaids.
Rose Tyler may have not done too well in school, but she's certainly holding her own in space. See them in Doctor Who.
Petyr Baelish's main assets? A sharp mind, deep pockets, and no scruples. See them in Game of Thrones.
Davos Seaworth is steadfast, intelligent, and trustworthy, which are hard traits to find in a place like Westeros. See them in Game of Thrones.
Shana is a red-haired warrior with a black-and-white worldview. See them in Shakugan no Shana.
More of a sex symbol than a crime-stopper, the original Silk Spectre has now become the ultimate superhero stage mom. See them in Watchmen.
With most of the people that Sango loved now gone, the only thing she wants is to kill the demon who destroyed her village. See them in Inuyasha.
Juno MacGuff is hoping sarcasm will get her through the stress of teenage life. And also, teenage pregnancy. See them in Juno.
With an abundant supply of alcohol, nice restaurants, and free will, Crowley is a demon who is thoroughly enjoying his time on Earth. See them in Good Omens: The Nice and Accurate Prophecies of Agnes Nutter, Witch.