Nothing spells “doom” like a first crush where life goes from really simple to really complicated in a heartbeat.  Once you’ve gotten over the initial awkward phase and the relationship starts to blossom, “doom” turns to love.

In writer-director Cameron Crowe’s hilarious directorial debut, Say Anything, the loveable, irrepressible Lloyd Dobler decides that he’s going to ask Diane Court out on a date.  He has the full support of his friends.

There’s just one obstacle:  Diane, the high school’s valedictorian, doesn’t know Lloyd exists.

No one knows Diane and she doesn’t know of the vagaries of high school social life.  You know, hanging out with friends?  Parties, maybe?  No, she knows none of that.  She’s lived a sheltered life, focusing on academics.

Lloyd doesn’t mind.  His friends try to warn him:  “She’s a brain caught in the body of a game show host.”

Featuring a dream ensemble cast including John Cusack, Ione Skye, John Mahoney, and Lili Taylor, Crowe crafted a script that is every bit as funny as Sixteen Candles and as serious as The Breakfast Club.  Can you tell we’re fans of John Hughes’ 80’s coming-of-age stories?

John Cusack is Lloyd Dobler, an underachieving army-brat who has no idea what to do with his life because his father, an Army lifer wants him to join.  “My father wants me to join the Army.  But I can’t work for that corporation.”  We know where his priorities lie.

Lloyd lives together with his sister, Constance, played by real-life sister Joan Cusack. Her son is the anchor for Lloyd’s life:  simple, playful, and funny.

Ione Skye is perfectly cast as the charmed, innocent Diane.  Her innocence is an important aspect of her relationship with her dad, the widower Jim, played with great sensitivity and practicality by John Mahoney.  Lili Taylor is absolutely awesome as the soulful songwriter, Corey Flood.  Corey has written 59 songs about Joe, a former crush of hers.  She finally gets over him.

Lloyd wins over Diane’s affections, but not before her own fable comes unglued with her dad, who it turns out is bilking retirees out of their retirement money in a Ponzi scheme.  In order to deal with the situation, Diane pushes Lloyd away.

Lloyd can’t accept this and in a signature moment in the film, Crowe and cinematographer László Kovács pan back on Lloyd holding a boombox above his head with Peter Gabriel’s “In Your Eyes” blaring through Diane’s open window.  Like everything else in this film, it is a perfect moment.

Maybe it’s too perfect.  The “will she, won’t she” bit towards the end of the film drags the conclusion out just a bit.  It’s not an editorial problem either.  Academy Award – nominated editor Richard Marks keeps the 100 minute run time on pace.

No.  The conflict seemed necessary for the characters to find resolution and acceptance.  Crowe deals through it with more humor as Lloyd recognizes there is a better part of himself because his heart is pure, “The rain on my car is a baptism. . . . . . Believe in myself.  Answer to no one.”

Jeremy Piven, Loren Dean, and Gregory Sporleder got their starts.  Bebe Neuwirth, Phillip Baker Hall, Eric Stoltz, Lois Chiles, and the future Homer Simpson, Dan Castellaneta all had memorable cameos.  It helps that James L. Brooks was an executive producer on the film.

Filled to the brim with memorable roles and moments, 20th Century Fox released Say Anything on April 14, 1989 in 1,113 screens.  Against a budget of $16 million, Cameron Crowe’s story of life, love, and romance would earn $21.5 million worldwide, topping many critics’ lists.

It was an instant hit with audiences’ too. 28 years later, Say Anything still resonates with its timeless themes and zany characters, especially the loveable Lloyd.