Best Drama Movies of 1999

1.

The Green Mile

7.1
8.6/10 IMDB

A supernatural tale set on death row in a Southern prison, where gentle giant John Coffey possesses the mysterious power to heal people's ailments. When the cell block's head guard, Paul Edgecomb, recognizes Coffey's miraculous gift, he tries desperately to help stave off the condemned man's execution.

Starring: Tom Hanks, Michael Clarke Duncan, David Morse, Bonnie Hunt, James Cromwell, Patricia Clarkson, Michael Jeter, Sam Rockwell, Graham Greene, Doug Hutchison ..
Directed by: Frank Darabont
Release date: 1999-12-10
2.

Fight Club

7.1
8.8/10 IMDB

A ticking-time-bomb insomniac and a slippery soap salesman channel primal male aggression into a shocking new form of therapy. Their concept catches on, with underground "fight clubs" forming in every town, until an eccentric gets in the way and ignites an out-of-control spiral toward oblivion.

Starring: Edward Norton, Brad Pitt, Helena Bonham Carter, Meat Loaf, Jared Leto, Zach Grenier, Holt McCallany, Eion Bailey, Richmond Arquette, David Andrews ..
Directed by: David Fincher
Release date: 1999-10-15
3.

The Sixth Sense

6.8
8.2/10 IMDB

Following an unexpected tragedy, a child psychologist named Malcolm Crowe meets an nine year old boy named Cole Sear, who is hiding a dark secret.

Starring: Bruce Willis, Toni Collette, Olivia Williams, Haley Joel Osment, Donnie Wahlberg, Glenn Fitzgerald, Mischa Barton, Trevor Morgan, Bruce Norris, Angelica Page ..
Directed by: M. Night Shyamalan
Release date: 1999-08-06
4.

American Beauty

6.8
8.4/10 IMDB

Lester Burnham, a depressed suburban father in a mid-life crisis, decides to turn his hectic life around after developing an infatuation with his daughter's attractive friend.

Starring: Kevin Spacey, Annette Bening, Thora Birch, Wes Bentley, Mena Suvari, Chris Cooper, Allison Janney, Peter Gallagher, Scott Bakula, Sam Robards ..
Directed by: Sam Mendes
Release date: 1999-09-15
5.

The Iron Giant

6.6
8.1/10 IMDB

In the small town of Rockwell, Maine in October 1957, a giant metal machine befriends a nine-year-old boy and ultimately finds its humanity by unselfishly saving people from their own fears and prejudices.

Starring: Eli Marienthal, Jennifer Aniston, Vin Diesel, Christopher McDonald, Harry Connick Jr., John Mahoney, Cloris Leachman, James Gammon, M. Emmet Walsh, Jack Angel ..
Directed by: Brad Bird
Release date: 1999-08-06
6.

The Straight Story

6.4
8.0/10 IMDB

A retired farmer and widower in his 70s, Alvin Straight learns one day that his distant brother Lyle has suffered a stroke and may not recover. Alvin is determined to make things right with Lyle while he still can, but his brother lives in Wisconsin, while Alvin is stuck in Iowa with no car and no driver's license. Then he hits on the idea of making the trip on his old lawnmower, thus beginning a picturesque and at times deeply spiritual odyssey.

Starring: Richard Farnsworth, Sissy Spacek, Jane Galloway Heitz, Joseph A. Carpenter, Donald Wiegert, Tracey Maloney, Dan Flannery, Ed Grennan, Jack Walsh, Gil Pearson ..
Directed by: David Lynch
Release date: 1999-10-15
7.

Magnolia

6.4
8.0/10 IMDB

An epic mosaic of many interrelated characters in search of happiness, forgiveness, and meaning in the San Fernando Valley.

Starring: Julianne Moore, William H. Macy, John C. Reilly, Tom Cruise, Philip Baker Hall, Philip Seymour Hoffman, Jason Robards, Alfred Molina, Melora Walters, Michael Bowen ..
Directed by: Paul Thomas Anderson
Release date: 1999-12-10
8.

The Insider

6.3
7.8/10 IMDB

Tells the true story of a 60 Minutes television series exposé of the tobacco industry, as seen through the eyes of a real tobacco executive, Jeffrey Wigand.

Starring: Al Pacino, Russell Crowe, Christopher Plummer, Diane Venora, Bruce McGill, Lindsay Crouse, Philip Baker Hall, Debi Mazar, Renee Olstead, Hallie Eisenberg ..
Directed by: Michael Mann
Release date: 1999-10-28
9.

October Sky

6.3
7.8/10 IMDB

Based on the true story of Homer Hickam, a coal miner's son who was inspired by the first Sputnik launch to take up rocketry against his father's wishes, and eventually became a NASA scientist.

Starring: Jake Gyllenhaal, Chris Cooper, Laura Dern, Chris Owen, William Lee Scott, Chad Lindberg, Natalie Canerday, Scott Miles, Randy Stripling, Chris Ellis ..
Directed by: Joe Johnston
Release date: 1999-02-19
10.

Tarzan

6.2
7.3/10 IMDB

Tarzan was a small orphan who was raised by an ape named Kala since he was a child. He believed that this was his family, but on an expedition Jane Porter is rescued by Tarzan. He then finds out that he's human. Now Tarzan must make the decision as to which family he should belong to...

Starring: Tony Goldwyn, Glenn Close, Minnie Driver, Brian Blessed, Nigel Hawthorne, Lance Henriksen, Wayne Knight, Alex D. Linz, Rosie O'Donnell, Taylor Dempsey ..
Directed by: Chris Buck, Kevin Lima
Release date: 1999-06-18
11.

Being John Malkovich

6.2
7.8/10 IMDB

One day at work, unsuccessful puppeteer Craig finds a portal into the head of actor John Malkovich. The portal soon becomes a passion for anybody who enters its mad and controlling world of overtaking another human body.

Starring: John Cusack, Cameron Diaz, Catherine Keener, John Malkovich, Charlie Sheen, Orson Bean, Mary Kay Place, W. Earl Brown, Carlos Jacott, Willie Garson ..
Directed by: Spike Jonze
Release date: 1999-10-29
12.

The Hurricane

6.2
7.6/10 IMDB

The story of Rubin "Hurricane" Carter, a boxer wrongly imprisoned for murder, and the people who aided in his fight to prove his innocence.

Starring: Denzel Washington, Vicellous Reon Shannon, Deborah Kara Unger, Liev Schreiber, John Hannah, Dan Hedaya, Debbi Morgan, Clancy Brown, David Paymer, Harris Yulin ..
Directed by: Norman Jewison
Release date: 1999-09-17
13.

Eyes Wide Shut

6.2
7.5/10 IMDB

After Dr. Bill Harford's wife, Alice, admits to having sexual fantasies about a man she met, Bill becomes obsessed with having a sexual encounter. He discovers an underground sexual group and attends one of their meetings -- and quickly discovers that he is in over his head.

Starring: Tom Cruise, Nicole Kidman, Madison Eginton, Jackie Sawiris, Sydney Pollack, Leslie Lowe, Peter Hans Benson, Todd Field, Michael Doven, Sky du Mont ..
Directed by: Stanley Kubrick
Release date: 1999-07-16
14.

Boys Don't Cry

6.1
7.5/10 IMDB

A young transgender man explores his gender identity and searches for love in rural Nebraska.

Starring: Hilary Swank, Chloë Sevigny, Peter Sarsgaard, Brendan Sexton III, Alicia Goranson, Alison Folland, Jeannetta Arnette, Rob Campbell, Matt McGrath, Cheyenne Rushing ..
Directed by: Kimberly Peirce
Release date: 1999-09-02
15.

10 Things I Hate About You

6.1
7.3/10 IMDB

On the first day at his new school, Cameron instantly falls for Bianca, the gorgeous girl of his dreams. The only problem is that Bianca is forbidden to date until her ill-tempered, completely un-dateable older sister Kat goes out, too. In an attempt to solve his problem, Cameron singles out the only guy who could possibly be a match for Kat: a mysterious bad boy with a nasty reputation of his own.

Starring: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik, David Krumholtz, Andrew Keegan, Susan May Pratt, Gabrielle Union, Larry Miller, Daryl Mitchell ..
Directed by: Gil Junger
Release date: 1999-03-30
16.

Girl, Interrupted

6.1
7.3/10 IMDB

Set in the changing world of the late 1960s, Susanna Kaysen's prescribed "short rest" from a psychiatrist she had met only once becomes a strange, unknown journey into Alice's Wonderland, where she struggles with the thin line between normal and crazy. Susanna soon realizes how hard it is to get out once she has been committed, and she ultimately has to choose between the world of people who belong inside or the difficult world of reality outside.

Starring: Winona Ryder, Angelina Jolie, Clea DuVall, Brittany Murphy, Elisabeth Moss, Vanessa Redgrave, Whoopi Goldberg, Jared Leto, Jeffrey Tambor, Travis Fine ..
Directed by: James Mangold
Release date: 1999-03-24
17.

Notting Hill

6.1
7.2/10 IMDB

William Thacker is a London bookstore owner whose humdrum existence is thrown into romantic turmoil when famous American actress Anna Scott appears in his shop. A chance encounter over spilled orange juice leads to a kiss that blossoms into a full-blown affair. As the average bloke and glamorous movie star draw closer and closer together, they struggle to reconcile their radically different lifestyles in the name of love.

Starring: Julia Roberts, Hugh Grant, Gina McKee, Tim McInnerny, Rhys Ifans, Emma Chambers, Hugh Bonneville, Richard McCabe, James Dreyfus, Dylan Moran ..
Directed by: Roger Michell
Release date: 1999-05-21
18.

Man on the Moon

6.1
7.4/10 IMDB

The story of the life and career of eccentric avant-garde comedian, Andy Kaufman.

Starring: Jim Carrey, Courtney Love, Bob Zmuda, Danny DeVito, Gerry Becker, Leslie Lyles, Greyson Erik Pendry, George Shapiro, Vincent Schiavelli, Paul Giamatti ..
Directed by: Miloš Forman
Release date: 1999-12-22
19.

Sleepy Hollow

6.1
7.3/10 IMDB

New York detective Ichabod Crane is sent to Sleepy Hollow to investigate a series of mysterious deaths in which the victims are found beheaded. Locals believe the culprit to be none other than the legendary Headless Horseman.

Starring: Johnny Depp, Ian McDiarmid, Christina Ricci, Casper Van Dien, Michael Gough, Christopher Walken, Lisa Marie, Steven Waddington, Christopher Lee, Miranda Richardson ..
Directed by: Tim Burton
Release date: 1999-11-19
20.

Following

6.0
7.5/10 IMDB

Bill, an idle, unemployed aspiring writer, walks the crowded streets of London following randomly chosen strangers, a seemingly innocent entertainment that becomes dangerous when he crosses paths with a mysterious character.

Starring: Jeremy Theobald, Alex Haw, Lucy Russell, John Nolan, Dick Bradsell, Gillian El-Kadi, Jennifer Angel, Nicolas Carlotti, Darren Ormandy, Guy Greenway ..
Directed by: Christopher Nolan
Release date: 1999-04-02
21.

The Talented Mr. Ripley

6.0
7.4/10 IMDB

Tom Ripley is a calculating young man who believes it's better to be a fake somebody than a real nobody. Opportunity knocks in the form of a wealthy U.S. shipbuilder who hires Tom to travel to Italy to bring back his playboy son, Dickie. Ripley worms his way into the idyllic lives of Dickie and his girlfriend, plunging into a daring scheme of duplicity, lies and murder.

Starring: Matt Damon, Gwyneth Paltrow, Jude Law, Cate Blanchett, Philip Seymour Hoffman, Jack Davenport, James Rebhorn, Sergio Rubini, Philip Baker Hall, Celia Weston ..
Directed by: Anthony Minghella
Release date: 1999-12-25
22.

The Virgin Suicides

5.9
7.2/10 IMDB

A group of male friends become obsessed with five mysterious sisters who are sheltered by their strict, religious parents.

Starring: Kirsten Dunst, Josh Hartnett, A.J. Cook, James Woods, Kathleen Turner, Leslie Hayman, Hanna Hall, Chelse Swain, Jonathan Tucker, Noah "40" Shebib ..
Directed by: Sofia Coppola
Release date: 1999-12-31
23.

Bicentennial Man

5.8
6.9/10 IMDB

Richard Martin buys a gift, a new NDR-114 robot. The product is named Andrew by the youngest of the family's children. "Bicentennial Man" follows the life and times of Andrew, a robot purchased as a household appliance programmed to perform menial tasks. As Andrew begins to experience emotions and creative thought, the Martin family soon discovers they don't have an ordinary robot.

Starring: Robin Williams, Sam Neill, Embeth Davidtz, Oliver Platt, Kiersten Warren, Wendy Crewson, Bradley Whitford, Lindze Letherman, Angela Landis, John Michael Higgins ..
Directed by: Chris Columbus
Release date: 1999-12-17
24.

Payback

5.8
7.1/10 IMDB

With friends like these, who needs enemies? That's the question bad guy Porter is left asking after his wife and partner steal his heist money and leave him for dead -- or so they think. Five months and an endless reservoir of bitterness later, Porter's partners and the crooked cops on his tail learn how bad payback can be.

Starring: Mel Gibson, Kris Kristofferson, Gregg Henry, Maria Bello, David Paymer, Bill Duke, Deborah Kara Unger, John Glover, William Devane, Lucy Liu ..
Directed by: Brian Helgeland
Release date: 1999-02-05
25.

Any Given Sunday

5.7
6.9/10 IMDB

A star quarterback gets knocked out of the game and an unknown third stringer is called in to replace him. The unknown gives a stunning performance and forces the ageing coach to reevaluate his game plans and life. A new co-owner/president adds to the pressure of winning. The new owner must prove herself in a male dominated world.

Starring: Al Pacino, Cameron Diaz, Dennis Quaid, James Woods, Jamie Foxx, LL Cool J, Matthew Modine, Jim Brown, Lawrence Taylor, Bill Bellamy ..
Directed by: Oliver Stone
Release date: 1999-12-22
26.

The Bone Collector

5.6
6.7/10 IMDB

Rookie cop, Amelia Donaghy reluctantly teams with Lincoln Rhyme – formerly the department's top homicide detective but now paralyzed as a result of a spinal injury – to catch a grisly serial killer dubbed 'The Bone Collector'. The murderer's special signature is to leave tantalizing clues based on the grim remains of his crimes.

Starring: Denzel Washington, Angelina Jolie, Queen Latifah, Michael Rooker, Michael McGlone, Luis Guzmán, Leland Orser, John Benjamin Hickey, Bobby Cannavale, Ed O'Neill ..
Directed by: Phillip Noyce
Release date: 1999-11-04
27.

Cruel Intentions

5.6
6.8/10 IMDB

Slaking a thirst for dangerous games, Kathryn challenges her stepbrother, Sebastian, to deflower their headmaster's daughter before the summer ends. If he succeeds, the prize is the chance to bed Kathryn. But if he loses, Kathryn will claim his most prized possession.

Starring: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair, Louise Fletcher, Joshua Jackson, Eric Mabius, Sean Patrick Thomas, Christine Baranski, Alaina Reed Hall ..
Directed by: Roger Kumble
Release date: 1999-03-05
28.

Double Jeopardy

5.4
6.5/10 IMDB

Framed for the slaying of her husband and sent to prison, Libby Parsons gets out on parole with one thing on her mind: revenge.

Starring: Tommy Lee Jones, Ashley Judd, Bruce Greenwood, Annabeth Gish, Benjamin Weir, Jay Brazeau, John Maclaren, Tracy Vilar, George Gordon, Spencer Treat Clark ..
Directed by: Bruce Beresford
Release date: 1999-09-24
29.

Ghost Dog: The Way of the Samurai

5.4
7.5/10 IMDB

An African-American Mafia hit man who models himself after the samurai of old finds himself targeted for death by the mob. Jarmusch's spiritual gangster film tells the story of an inner-city hit man (Whitaker) who lives on a rooftop, training himself as a samurai in the strictest sense. He communicates primarily by carrier pigeon, while remaining loyal to a gangster (Tormey) who once saved his life.

Starring: Forest Whitaker, Cliff Gorman, Tricia Vessey, Henry Silva, Victor Argo, Joseph Rigano, Vince Viverito, John Tormey, Damon Whitaker, Frank Minucci ..
Directed by: Jim Jarmusch
Release date: 1999-06-02
30.

Angela's Ashes

5.4
7.3/10 IMDB

Based on the best selling autobiography by Irish expat Frank McCourt, Angela's Ashes follows the experiences of young Frankie and his family as they try against all odds to escape the poverty endemic in the slums of pre-war Limerick. The film opens with the family in Brooklyn, but following the death of one of Frankie's siblings, they return home, only to find the situation there even worse. Prejudice against Frankie's Northern Irish father makes his search for employment in the Republic difficult despite his having fought for the IRA, and when he does find money, he spends the money on drink.

Starring: Emily Watson, Robert Carlyle, Joe Breen, Michael Legge, Ciaran Owens, J.J. Murphy, Johnny Murphy, Ronnie Masterson, Pauline McLynn, Liam Carney ..
Directed by: Alan Parker
Release date: 1999-12-25
31.

Big Daddy

5.3
6.4/10 IMDB

A lazy law school grad adopts a kid to impress his girlfriend, but everything doesn't go as planned and he becomes the unlikely foster father.

Starring: Adam Sandler, Joey Lauren Adams, Kristy Swanson, Cole Sprouse, Jon Stewart, Leslie Mann, Allen Covert, Rob Schneider, Peter Dante, Steve Buscemi ..
Directed by: Dennis Dugan
Release date: 1999-06-25
32.

The Messenger: The Story of Joan of Arc

5.3
6.4/10 IMDB

In 1429 a teenage girl from a remote French village stood before her King with a message she claimed came from God; that she would defeat the world's greatest army and liberate her country from its political and religious turmoil. Following her mission to reclaim god's diminished kingdom - through her amazing victories until her violent and untimely death.

Starring: Milla Jovovich, Dustin Hoffman, Faye Dunaway, John Malkovich, Vincent Cassel, Tchéky Karyo, Rab Affleck, Stéphane Algoud, Edwin Apps, David Bailie ..
Directed by: Luc Besson
Release date: 1999-10-27
33.

Ratcatcher

5.3
7.5/10 IMDB

James Gillespie is 12 years old. The world he knew is changing. Haunted by a secret, he has become a stranger in his own family. He is drawn to the canal where he creates a world of his own. He finds an awkward tenderness with Margaret Anne, a vulnerable 14 year old expressing a need for love in all the wrong ways, and befriends Kenny, who possesses an unusual innocence in spite of the harsh surroundings.

Starring: William Eadie, Tommy Flanagan, Mandy Matthews, Michelle Stewart, Lynne Ramsay Jr., Leanne Mullen, John Miller, Jackie Quinn, James Ramsay, Anne McLean ..
Directed by: Lynne Ramsay
Release date: 1999-11-12
34.

Entrapment

5.3
6.3/10 IMDB

Two thieves, who travel in elegant circles, try to outsmart each other and, in the process, end up falling in love.

Starring: Sean Connery, Catherine Zeta-Jones, Will Patton, Maury Chaykin, Ving Rhames, Kevin McNally, Terry O'Neill, Madhav Sharma, David Yip, Tim Potter ..
Directed by: Jon Amiel
Release date: 1999-04-29
35.

The Cider House Rules

5.3
7.4/10 IMDB

Homer is an orphan who was never adopted, becoming the favorite of orphanage director Dr. Larch. Dr. Larch imparts his full medical knowledge on Homer, who becomes a skilled, albeit unlicensed, physician. But Homer yearns for a self-chosen life outside the orphanage. What will Homer learn about life and love in the cider house? What of the destiny that Dr. Larch has planned for him?

Starring: Tobey Maguire, Charlize Theron, Delroy Lindo, Paul Rudd, Michael Caine, Jane Alexander, Kathy Baker, Erykah Badu, Kieran Culkin, Kate Nelligan ..
Directed by: Lasse Hallström
Release date: 1999-12-17
Best Drama Movies of 1999 : Sunshine
36.

Sunshine

5.2
7.5/10 IMDB

The story of a Jewish family living in Hungary—through three generations—rising from humble beginnings to positions of wealth and power in the crumbling Austro-Hungarian Empire. The patriarch becomes a prominent judge but is torn when his government sanctions anti-Jewish persecutions. His son converts to Christianity to advance his career as a champion fencer and Olympic hero, but is caught up in the Holocaust. Finally, the grandson, after surviving war, revolution, loss and betrayal, realizes that his ultimate allegiance must be to himself and his heritage.

Starring: Ralph Fiennes, William Hurt, Rachel Weisz, Miriam Margolyes, Rüdiger Vogler, Hanns Zischler, Katja Studt, John Neville, James Frain, Molly Parker ..
Directed by: István Szabó
Release date: 1999-09-13
37.

Arlington Road

5.2
7.2/10 IMDB

Threats from sinister foreign nationals aren't the only thing to fear. Bedraggled college professor Michael Faraday has been vexed (and increasingly paranoid) since his wife's accidental death in a botched FBI operation. But all that takes a backseat when a seemingly all-American couple set up house next door.

Starring: Jeff Bridges, Tim Robbins, Joan Cusack, Hope Davis, Robert Gossett, Mason Gamble, Spencer Treat Clark, Stanley Anderson, Viviane Vives, Lee Stringer ..
Directed by: Mark Pellington
Release date: 1999-03-19
38.

The War Zone

5.1
7.3/10 IMDB

An alienated teenager, saddened that he has moved away from London, must find a way to deal with a dark family secret.

Starring: Ray Winstone, Tilda Swinton, Lara Belmont, Colin Farrell, Freddie Cunliffe, Kate Ashfield, Aisling O'Sullivan, Megan Thorp, Kim Wall, Annabelle Apsion ..
Directed by: Tim Roth
Release date: 1999-06-11
39.

Pirates of Silicon Valley

5.1
7.2/10 IMDB

The story about the men who made the world of technology what it is today, their struggles during college, the founding of their companies, and the ingenious actions they took to build up the global corporate empires of Apple Computer Inc. and Microsoft Corporation.

Starring: Noah Wyle, Joey Slotnick, J.G. Hertzler, Anthony Michael Hall, Wayne Pére, Sheila Shaw, Gema Zamprogna, John DiMaggio, Josh Hopkins, Gailard Sartain ..
Directed by: Martyn Burke
Release date: 1999-05-10
40.

Human Traffic

5.1
7.1/10 IMDB

Five twenty-something friends spend a drug-fueled weekend in Cardiff, Wales.

Starring: John Simm, Shaun Parkes, Nicola Reynolds, Lorraine Pilkington, Danny Dyer, Dean Davies, Andrew Lincoln, Terence Beesley, Jo Brand, Richard Coyle ..
Directed by: Justin Kerrigan
Release date: 1999-06-04
41.

Topsy-Turvy

5.0
7.4/10 IMDB

After their production "Princess Ida" meets with less-than-stunning reviews, the relationship between Gilbert and Sullivan is strained to breaking. Their friends and associates attempt to get the two to work together again, which opens the way to "The Mikado," one of the duo's greatest successes.

Starring: Allan Corduner, Jim Broadbent, Timothy Spall, Dexter Fletcher, Shirley Henderson, Lesley Manville, Ron Cook, Andy Serkis, Wendy Nottingham, Kevin McKidd ..
Directed by: Mike Leigh
Release date: 1999-12-15
42.

Sweet and Lowdown

5.0
7.2/10 IMDB

A comedic biopic focused on the life of fictional jazz guitarist Emmett Ray. Ray was an irresponsible, free-spending, arrogant, obnoxious, alcohol-abusing, miserable human being, who was also arguably the best guitarist in the world.

Starring: Woody Allen, Ben Duncan (DJ), Daniel Okrent, Dan Moran, Tony Darrow, Chris Bauer, Sean Penn, Darryl Alan Reed, James Urbaniak, Uma Thurman ..
Directed by: Woody Allen
Release date: 1999-12-03
43.

Anna and the King

5.0
6.7/10 IMDB

The story of the romance between the King of Siam (now Thailand) and the widowed British school teacher Anna Leonowens during the 1860s. Anna teaches the children and becomes romanced by the King. She convinces him that a man can be loved by just one woman.

Starring: Jodie Foster, Chow Yun-Fat, Bai Ling, Tom Felton, Geoffrey Palmer, Randall Duk Kim, Lim Kay Siu, Melissa Campbell, Keith Chin, Mano Maniam ..
Directed by: Andy Tennant
Release date: 1999-12-16
44.

Titus

5.0
7.1/10 IMDB

Titus Andronicus returns from the wars and sees his sons and daughters taken from him, one by one. Shakespeare's goriest and earliest tragedy.

Starring: Anthony Hopkins, Jessica Lange, Jonathan Rhys Meyers, Matthew Rhys, Osheen Jones, Dario D'Ambrosi, Raz Degan, Harry Lennix, Angus Macfadyen, Kenny Doughty ..
Directed by: Julie Taymor
Release date: 1999-12-25
45.

Never Been Kissed

5.0
6.0/10 IMDB

Josie Geller, a baby-faced junior copywriter at the Chicago Sun-Times, must pose as a student at her former high school to research contemporary teenage culture. With the help of her brother, Rob, Josie infiltrates the inner circle of the most popular clique on campus. But she hits a major snag in her investigation -- not to mention her own failed love life -- when she falls for her dreamy English teacher, Sam Coulson.

Starring: Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon, Jenny Bicks, Jessica Alba, John C. Reilly, James Franco, Octavia Spencer, Garry Marshall ..
Directed by: Raja Gosnell
Release date: 1999-04-09
46.

The End of the Affair

5.0
7.0/10 IMDB

On a rainy London night in 1946, novelist Maurice Bendrix has a chance meeting with Henry Miles, husband of his ex-mistress Sarah, who abruptly ended their affair two years before. Bendrix's obsession with Sarah is rekindled; he succumbs to his own jealousy and arranges to have her followed.

Starring: Ralph Fiennes, Stephen Rea, Julianne Moore, James Bolam, Ian Hart, Jason Isaacs, Deborah Findlay, Sam Bould, Cyril Shaps, Simon Turner ..
Directed by: Neil Jordan
Release date: 1999-12-03
47.

The Limey

5.0
6.9/10 IMDB

The Limey follows Wilson, a tough English ex-con who travels to Los Angeles to avenge his daughter's death. Upon arrival, Wilson goes to task battling Valentine and an army of L.A.'s toughest criminals, hoping to find clues and piece together what happened. After surviving a near-death beating, getting thrown from a building and being chased down a dangerous mountain road, the Englishman decides to dole out some bodily harm of his own.

Starring: Terence Stamp, Lesley Ann Warren, Luis Guzmán, Barry Newman, Joe Dallesandro, Nicky Katt, Peter Fonda, Amelia Heinle, Melissa George, William Lucking ..
Directed by: Steven Soderbergh
Release date: 1999-05-15
Best Drama Movies of 1999 : Mulholland Dr.
48.

Mulholland Dr.

5.0
8.2/10 IMDB

Initially, "Mulholland Dr." was to mark David Lynch's return to television. It is a retooling of a script originally shot as a 94-minute pilot for a TV series (co-written with TV screenwriter Joyce Eliason) for the channel ABC, which had approved the script, but chose not even to air the pilot once it was done in 1999, despite Lynch's labours to cut the project to their liking. It was left in limbo until 18 month later French company Studio Canal Plus (also producer of 'The Straight Story') agreed to pay ABC $7 million for the pilot, and budget a few million more to turn the pilot into a two-hour, 27-minute movie. The cost of the film doubled to $14 million as sets had to be reconstructed and actors recalled.

Starring: Justin Theroux, Naomi Watts, Laura Harring, Ann Miller, Robert Forster, Angelo Badalamenti, Brent Briscoe, Scott Coffey, Katharine Towne, Dan Hedaya ..
Directed by: David Lynch
Release date: 1999-01-01
49.

East Is East

4.9
6.9/10 IMDB

In 1971 Salford fish-and-chip shop owner George Khan expects his family to follow his strict Pakistani Muslim ways. But his children, with an English mother and having been born and brought up in Britain, increasingly see themselves as British and start to reject their father's rules on dress, food, religion, and living in general.

Starring: Om Puri, Linda Bassett, Ian Aspinall, Jimi Mistry, Archie Panjabi, Jordan Routledge, Chris Bisson, Lesley Nicol, Emil Marwa, Raji James ..
Directed by: Damien O'Donnell
Release date: 1999-05-14
50.

The Thomas Crown Affair

4.9
6.8/10 IMDB

A very rich and successful playboy amuses himself by stealing artwork, but may have met his match in a seductive detective.

Starring: Pierce Brosnan, Rene Russo, Denis Leary, Ben Gazzara, Frankie Faison, Fritz Weaver, Charles Keating, Mark Margolis, Faye Dunaway, Michael Lombard ..
Directed by: John McTiernan
Release date: 1999-08-06

Also check Best drama movies of 2000.

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