I’m a James Spader fan from way back. I would say as far back as Tuff Turf (1985), but I technically didn’t see that movie until a couple of years ago, so I guess Pretty in Pink (1986) was my actual starting point — with his first sleazy line as yuppie asshole Steff, I was smitten. Everyone else loved Jon Cryer’s Duckie or Andrew McCarthy’s Blaine (as did I, to an extent), but it was Steff that I adored the most. I can’t say I understood the complexities of the character — or Spader’s performance — as a nine-year-old, but I was drawn to “bad boys” even then.

In the next few Spader movies I saw (Mannequin, Less Than Zero, Baby Boom), he continued his trend of playing smarmy prick characters, none of whom were likable at all. Then, one night when I was about 11 or 12, I snuck downstairs and watched Sex, Lies and Videotape (1989) on cable, and that was it — his performance in Steven Soderbergh’s directorial debut made me a fan for life. I’ve seen almost every film Spader’s made since then, good or bad (he’s done his fair share of shitty films), and one of my favorites, hands down, is Secretary (2002).

Most critics consider it to be Maggie Gyllenhaal’s breakthrough film. I agree — while she had already been in several films prior to Secretary, it was her performance as the masochistic title character that really put her on the map. (Fun fact: Gwyneth Paltrow was originally cast in the role. Can you imagine?) However, I also like to think of it as something of a comeback vehicle for Spader. I mean, after his performances in Stargate and Crash in the mid-’90s, his output was inconsistent and, well, pretty mediocre. I love you, Jimmy, but Slow Burn?

Directed by Steven Shainberg (not Soderbergh), Secretary is based on a short story by Mary Gaitskill and was the first film for screenwriter Erin Cressida Wilson, who won the Independent Spirit Award for Best First Screenplay. Gyllenhaal plays Lee Holloway, a young woman from a dysfunctional family who returns home after spending time in a mental hospital because of an “incident” with a kitchen knife.

In an attempt to lead a normal life, Lee takes typing classes at a community college and begins dating a high school acquaintance named Peter (Jeremy Davies). Eventually she starts looking for a job and decides to answer an ad for a secretary; her unconventional interview with eccentric lawyer E. Edward Grey (Spader) ends with her being offered the position. Edward is at once annoyed and turned on by Lee’s awkwardness and the many mistakes she makes as his new secretary. After noticing that she’s a “cutter,” he confronts her about her addiction to self-harm and tells her she will never hurt herself again. The exchange excites them both, and they soon begin a sadomasochistic, though sexless, relationship.

But Edward begins to feel self-conscious and ashamed of his relationship with Lee, and after a sexual encounter in his office, he fires her. She’s hurt and dejected, but determined to get on with her life and not throw away her newly discovered self-confidence. She continues to date Peter and even accepts his proposal of marriage. But as she’s trying on Peter’s mother’s wedding gown, she realizes that the man she really wants is Edward, so she runs off to confront him. To prove her love, she obeys his order to sit at his desk, without moving, until he returns. A few days later he does, and the two realize they were meant to be together.

Secretary‘s soundtrack is just as quirky and nuanced as the film itself. Composed by longtime David Lynch collaborator Angelo Badalamenti, the score has a dreamy yet dark quality that is decidedly Badalamenti. The official soundtrack album also includes songs by Leonard Cohen and Lizzie West that are pivotal to the film’s mood. (Another fun fact: on West’s track, “Chariots Rise,” the line “What a fool am I to fall so in love” was changed to “What grace have I, to fall so in love” at Shainberg’s request.)

The rest of the songs featured in the film range from modern rock to modern lounge, and I’ve managed to find all but one of them — “It’s So Strange (The Way Love Works)” by the Honeydogs.

Angelo Badalamenti – Main Title
Angelo Badalamenti – Feelin’ Free
Angelo Badalamenti – Snow Dome Dreams
Angelo Badalamenti – Bathing Blossom
Angelo Badalamenti – Seeing Scars
Angelo Badalamenti – Loving to Obey
Angelo Badalamenti – Office Obligations
Angelo Badalamenti – The Loving Tree
Angelo Badalamenti – Orchids
Angelo Badalamenti – Secretary’s Secrets
Esquivel – Whatchamacallit
War – Me and Baby Brother
Little Richard – Directly From My Heart to You
The Seeds – Can’t Seem to Make You Mine
Rolley Polley – Blue Rumba
Combustible Edison – Vertigogo
James Taylor Quartet – Music to Watch Girls By
Pete Belasco – All I Want
Leonard Cohen – I’m Your Man
The Januaries – Summer of Love
The Faint – Agenda Suicide
Cake – I Will Survive
Oranger – A View of the City From an Airplane
Iffy – Georgina
Lizzie West – Chariots Rise