The 15th Independent Spirit Awards, honoring the best in independent filmmaking for 1999, were announced on March 25, 2000. It was hosted by Jennifer Tilly.
Nominees and winners
{ | class="wikitable" !Best Feature !Best Director |- |Election
Cookie's Fortune
The Limey
The Straight Story
Sugar Town
|Alexander Payne – Election
Harmony Korine – Julien Donkey-Boy
Doug Liman – Go
David Lynch – The Straight Story
Steven Soderbergh – The Limey
|-
!Best Male Lead
!Best Female Lead
|-
|Richard Farnsworth – The Straight Story
John Cusack – Being John Malkovich
Terence Stamp – The Limey
David Strathairn – Limbo
Noble Willingham – The Corndog Man
|Hilary Swank – Boys Don't Cry
Diane Lane – A Walk on the Moon
Janet McTeer – Tumbleweeds
Susan Traylor – Valerie Flake
Reese Witherspoon – Election
|-
!Best Supporting Male
!Best Supporting Female
|-
|Steve Zahn – Happy, Texas
Charles S. Dutton – Cookie's Fortune
Clark Gregg – The Adventures of Sebastian Cole
Luis Guzmán – The Limey
Terrence Howard – The Best Man
|Chloë Sevigny – Boys Don't Cry
Barbara Barrie – Judy Berlin
Vanessa Martinez – Limbo
Sarah Polley – Go
Jean Smart – Guinevere
|-
!Best Screenplay
!Best First Screenplay
|-
|Election – Alexander Payne and Jim Taylor Dogma – Kevin Smith
Guinevere – Audrey Wells
The Limey – Lem Dobbs
SLC Punk! – James Merendino
|Being John Malkovich – Charlie Kaufman The Adventures of Sebastian Cole – Kip Williams Boys Don't Cry – Kimberly Peirce and Andy Bienen Cookie's Fortune – Anne Rapp The Straight Story – John Roach and Mary Sweeney |- !Best Cinematography !Best Debut Performance |- |Three Seasons – Lisa Rinzler The City – Harlan Bosmajian Judy Berlin – Jeffrey Seckendorf Julien Donkey-Boy – Anthony Dod Mantle Twin Falls Idaho – M. David Mullen |Kimberly J. Brown – Tumbleweeds
Jessica Campbell – Election
Jade Gordon – Sugar Town
Toby Smith – Drylongso
Chris Stafford – Edge of Seventeen
|-
!Best First Feature (Over $500,000) !Best First Feature (Under $500,000) |- |Being John Malkovich