1. St. Elmo's Fire
Date: 1985
Starring: Rob Lowe, Demi Moore, Emilio Estevez, Andrew McCarthy (whatever happened to him?), Judd Nelson, Ally Sheedy, Andie MacDowell
Reason to watch it: Rob Lowe. You don't need another reason.
St. Elmo's Fire could also be called a darker, more twisted version of Friends - without the canned laughter. A group of pals sleep with each other, whine to each other, screw each other over and try to help each other make sense of adult life at the tender ages of 21 and 22.
Wannabe rich boy Emilio has a crush on Andie, the doctor. Rob is a screw-up with a chip on his shoulder from drug deals gone bad. Demi is at her raspy - and slutty - best. Judd and Ally grapple with commitment, and Andrew, who Judd thinks is gay, is in love with Ally but too shy to make a move. Got it? If not, then rent it again. You won't regret it.

2. The Legend of Billie Jean
Date: 1986
Starring: Helen Slater, Christian Slater
Reason to watch it: Teenage outlaws!
A nice, endearing story about two trailer-park siblings who get picked on by the town bully and his dad over - you guessed it - a scooter. Rather than settling the argument rationally, Billie Jean takes matters into her own hands and becomes the new national hero and spokeswoman for teenage injustice. Some may call her the modern-day Joan of Arc.

3. The Breakfast Club
Date: 1985
Starring: Judd Nelson, Molly Ringwald, Emilio Estevez, Ally Sheedy, Anthony Michael Hall
Reason to watch it: To see Molly Ringwald put lipstick on with the help of her cleavage.
There's nothing like a little Judd, Molly, Anthony, Emilio and Ally on a rainy Sunday morning. You've got the rebel, the princess, the dork, the athlete and the loner, and you know as well as I do that some part of you can identify with each of these characters. You can also discuss the politics of Judd's rebellious nature and how he reminds you of some guy who's no good for you but is still on your mind.
Just think about the plot as one big blind date: five people in the same room who think they have nothing in common, getting to know one another regardless of social strata. It's an all-time classic with a pre-Suddenly Susan Judd Nelson. That means he's actually hot in the movie.

4. Say Anything
Date: 1989
Starring: John Cusack, Ione Skye, John Mahoney

Reason to watch it: John Cusack saying, 'I don't want to sell anything, buy anything or process anything as a career. I don't want to sell anything bought or processed… or buy anything sold or processed… or process anything sold, bought or processed… or repair anything sold, bought or processed. You know, as a career, I don't want to do that.'
Lloyd Dobler (Cusack), quintessential man at the age of 19, flustered young 'un in love with Diane (Skye), blends the perfect combo of eccentricity, love and forlornness, and he does it in such a way that you won't feel ashamed for watching a movie about a fumbling high school boy with a crush on a gorgeous girl.
What makes it even more difficult is Diane's father (Mahoney), who lives vicariously through his daughter's academic aspirations. Teen angst at its best. And John is just so damn lovable!

5. Purple Rain
Date: 1984
Starring: Prince, Apollonia
Reason to watch it: For goodness sake - it's Prince back when he was a real man with a real name!
The artist formerly known as The Artist Formerly Known as Prince -yup, we can call him by his given name again - was memorable as a struggling young bi-racial musician fighting his way toward recognition. You'd think his problems would start and end with hatching a music career, but he's also fighting for Apollonia, the beautiful vixen who's tempted by a more successful enemy band (and its lead singer) - even though she pawned her ankle bracelet so Prince could get his coveted guitar!
Prince must also grin and bear an abusive father and shattered mother. But forget about plot - it's the soundtrack that makes the movie.