Best Romance Movies of 1999

1.

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
2.

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
3.

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
4.

American Pie

5.6
7.0/10 IMDB

At a high-school party, four friends find that losing their collective virginity isn't as easy as they had thought. But they still believe that they need to do so before college. To motivate themselves, they enter a pact to all "score" by their senior prom.

Starring: Jason Biggs, Chris Klein, Thomas Ian Nicholas, Alyson Hannigan, Shannon Elizabeth, Tara Reid, Eddie Kaye Thomas, Seann William Scott, Eugene Levy, Natasha Lyonne ..
Directed by: Paul Weitz, Chris Weitz
Release date: 1999-07-09
5.

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
6.

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
7.

Election

5.2
7.3/10 IMDB

Jim McAllister, a well-liked high school government teacher, can't help but notice that successful student Tracy Flick uses less than ethical tactics to get what she wants. When Tracy runs for school president, Jim feels that she will be a poor influence on the student body and convinces Paul, a dim-witted but popular student athlete, to run against Tracy. When she becomes aware of Jim's secret involvement in the race, a bitter feud is sparked.

Starring: Matthew Broderick, Reese Witherspoon, Chris Klein, Jessica Campbell, Mark Harelik, Phil Reeves, Molly Hagan, Delaney Driscoll, Colleen Camp, Frankie Ingrassia ..
Directed by: Alexander Payne
Release date: 1999-04-23
8.

She's All That

5.0
5.9/10 IMDB

High school hotshot Zach Siler is the envy of his peers. But his popularity declines sharply when his cheerleader girlfriend, Taylor, leaves him for sleazy reality-television star Brock Hudson. Desperate to revive his fading reputation, Siler agrees to a seemingly impossible challenge. He has six weeks to gain the trust of nerdy outcast Laney Boggs -- and help her to become the school's next prom queen.

Starring: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard, Paul Walker, Jodi Lyn O'Keefe, Anna Paquin, Clea DuVall, Kieran Culkin, Kevin Pollak, Lil' Kim ..
Directed by: Robert Iscove
Release date: 1999-01-29
9.

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
10.

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
11.

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
12.

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
13.

Runaway Bride

4.9
5.6/10 IMDB

Ike Graham, New York columnist, writes his text always at the last minute. This time, a drunken man in his favourite bar tells Ike about Maggie Carpenter, a woman who always flees from her grooms in the last possible moment. Ike, who does not have the best opinion about females anyway, writes an offensive column without researching the subject thoroughly.

Starring: Julia Roberts, Richard Gere, Joan Cusack, Rita Wilson, Hector Elizondo, Christopher Meloni, Paul Dooley, Donal Logue, Sela Ward, Sandra Taylor ..
Directed by: Garry Marshall
Release date: 1999-07-30
14.

Mansfield Park

4.9
7.0/10 IMDB

When spirited young woman, Fanny Price is sent away to live on the great country estate of her rich cousins, she's meant to learn the ways of proper society. But while Fanny learns 'their' ways, she also enlightens them with a wit and sparkle all her own.

Starring: Frances O'Connor, Lindsay Duncan, James Purefoy, Sheila Gish, Harold Pinter, Victoria Hamilton, Hugh Bonneville, Justine Waddell, Embeth Davidtz, Alessandro Nivola ..
Directed by: Patricia Rozema
Release date: 1999-11-12
15.

For Love of the Game

4.9
6.6/10 IMDB

A baseball legend almost finished with his distinguished career at the age of forty has one last chance to prove who he is, what he is capable of, and win the heart of the woman he has loved for the past four years.

Starring: Kevin Costner, Kelly Preston, John C. Reilly, Jena Malone, J.K. Simmons, Brian Cox, David Mucci, Carmine Giovinazzo, Bill E. Rogers, Hugh Ross ..
Directed by: Sam Raimi
Release date: 1999-09-17
16.

Blast from the Past

4.9
6.7/10 IMDB

Following a bomb scare in the 1960s that locked the Webers into their bomb shelter for 35 years, Adam now ventures forth into Los Angeles to obtain food and supplies for his family, and a non-mutant wife for himself.

Starring: Brendan Fraser, Alicia Silverstone, Christopher Walken, Sissy Spacek, Nathan Fillion, Dave Foley, Joey Slotnick, Mary Ann Hermansen, Deborah Kellner, Don Yesso ..
Directed by: Hugh Wilson
Release date: 1999-02-12
17.

An Ideal Husband

4.8
6.8/10 IMDB

Sir Robert Chiltern is a successful government minister, well-off and with a loving wife. All this is threatened when Mrs Cheveley appears in London with damning evidence of a past misdeed. Sir Robert turns for help to his friend Lord Goring, an apparently idle philanderer and the despair of his father. Goring knows the lady of old, and, for him, takes the whole thing pretty seriously.

Starring: Cate Blanchett, Minnie Driver, Rupert Everett, Julianne Moore, Jeremy Northam, Peter Vaughan, Ben Pullen, Marsha Fitzalan, Lindsay Duncan, John Wood ..
Directed by: Oliver Parker
Release date: 1999-04-15
18.

Summer of Sam

4.8
6.7/10 IMDB

Spike Lee's take on the "Son of Sam" murders in New York City during the summer of 1977 centering on the residents of an Italian-American South Bronx neighborhood who live in fear and distrust of one another.

Starring: John Leguizamo, Adrien Brody, Mira Sorvino, Jennifer Esposito, Michael Rispoli, Saverio Guerra, Brian Tarantina, Al Palagonia, Ken Garito, Bebe Neuwirth ..
Directed by: Spike Lee
Release date: 1999-07-02
19.

Ride with the Devil

4.8
6.7/10 IMDB

Ride with the Devil follows four people who are fighting for truth and justice amidst the turmoil of the American Civil War. Director Ang Lee takes us to a no man's land on the Missouri/Kansas border where a staunch loyalist, an immigrant's son, a freed slave, and a young widow form an unlikely friendship as they learn how to survive in an uncertain time. In a place without rules and redefine the meaning of bravery and honor.

Starring: Tobey Maguire, Skeet Ulrich, Jeffrey Wright, Jewel, Jonathan Rhys Meyers, Jim Caviezel, Simon Baker, Tom Wilkinson, John Judd, Don Shanks ..
Directed by: Ang Lee
Release date: 1999-11-24
20.

A Midsummer Night's Dream

4.7
6.4/10 IMDB

A film adaptation of Shakespeare's comedy about lovers whose romantic affections are manipulated by fairy magic. The setting is updated to a Tuscan hill town in the late 19th century.

Starring: Rupert Everett, Calista Flockhart, Kevin Kline, Michelle Pfeiffer, Stanley Tucci, Christian Bale, Sophie Marceau, David Strathairn, Anna Friel, Dominic West ..
Directed by: Michael Hoffman
Release date: 1999-05-14
21.

Message in a Bottle

4.6
6.2/10 IMDB

A woman finds a romantic letter in a bottle washed ashore and tracks down the author, a widowed shipbuilder whose wife died tragically early. As a deep and mutual attraction blossoms, the man struggles to make peace with his past so that he can move on and find happiness.

Starring: Kevin Costner, Robin Wright, Paul Newman, John Savage, Illeana Douglas, Robbie Coltrane, Jesse James, Bethel Leslie, Tom Aldredge, Viveka Davis ..
Directed by: Luis Mandoki
Release date: 1999-02-22
22.

Snow Falling on Cedars

4.6
6.7/10 IMDB

In the 1950s, a Japanese-American fisherman is suspected of killing his neighbour at sea — and race is a factor in the trial. So is reporter, Ishmael.

Starring: Ethan Hawke, Youki Kudoh, Reeve Carney, Anne Suzuki, Rick Yune, Max von Sydow, James Rebhorn, James Cromwell, Richard Jenkins, Arija Bareikis ..
Directed by: Scott Hicks
Release date: 1999-12-22
23.

Varsity Blues

4.6
6.5/10 IMDB

In small-town Texas, high school football is a religion, 17-year-old schoolboys carry the hopes of an entire community onto the gridiron every Friday night. When star quarterback Lance Harbor suffers an injury, the Coyotes are forced to regroup under the questionable leadership of John Moxon, a second-string quarterback with a slightly irreverent approach to the game.

Starring: James Van Der Beek, Amy Smart, Jon Voight, Paul Walker, Ron Lester, Scott Caan, Ali Larter, Richard Lineback, Thomas F. Duffy, Joe Pichler ..
Directed by: Brian Robbins
Release date: 1999-01-15
Best Romance Movies of 1999 : The Other Sister
24.

The Other Sister

4.6
6.4/10 IMDB

A mentally challenged girl proves herself to be every bit as capable as her "perfect" sister when she moves into an apartment and begins going to college.

Starring: Juliette Lewis, Diane Keaton, Tom Skerritt, Giovanni Ribisi, Poppy Montgomery, Sarah Paulson, Linda Thorson, Joe Flanigan, Juliet Mills, Tracy Reiner ..
Directed by: Garry Marshall
Release date: 1999-02-26
25.

Anywhere but Here

4.5
6.2/10 IMDB

Single mother Adele August is bad with money, and even worse when it comes to making decisions. Her straight-laced daughter, Ann, is a successful high school student with Ivy League aspirations. When Adele decides to pack up and move the two of them from the Midwest to Beverly Hills, Calif., to pursue her dreams of Hollywood success, Ann grows frustrated with her mother's irresponsible and impulsive ways.

Starring: Susan Sarandon, Natalie Portman, Hart Bochner, Eileen Ryan, Ray Baker, John Diehl, Shawn Hatosy, Bonnie Bedelia, Faran Tahir, Shishir Kurup ..
Directed by: Wayne Wang
Release date: 1999-11-12
26.

The Story of Us

4.5
5.9/10 IMDB

Ben and Katie Jordan are a married couple who go through hard times in fifteen years of marriage.

Starring: Bruce Willis, Michelle Pfeiffer, Rob Reiner, Colleen Rennison, Jake Sandvig, Casey Boersma, Julie Hagerty, Rita Wilson, Paul Reiser, Red Buttons ..
Directed by: Rob Reiner
Release date: 1999-10-14
27.

Drive Me Crazy

4.4
5.7/10 IMDB

Nicole and Chase live next door to each other but are worlds apart. However, they plot a scheme to date each other in order to attract the interest and jealousy of their respective romantic prey. But in the mist of planning a gala centennial celebration, Nicole and Chase find that the one they always wanted was closer than they ever thought.

Starring: Melissa Joan Hart, Stephen Collins, Adrian Grenier, Susan May Pratt, Ali Larter, Keri Lynn Pratt, Mark Metcalf, William Converse-Roberts, Faye Grant, Kris Park ..
Directed by: John Schultz
Release date: 1999-10-01
28.

Mickey Blue Eyes

4.4
5.9/10 IMDB

An English auctioneer proposes to the daughter of a mafia kingpin, only to realize that certain "favors" would be asked of him.

Starring: Hugh Grant, James Caan, Jeanne Tripplehorn, Burt Young, James Fox, Joe Viterelli, Gerry Becker, Maddie Corman, Tony Darrow, Paul Lazar ..
Directed by: Kelly Makin
Release date: 1999-08-16
29.

200 Cigarettes

4.4
5.9/10 IMDB

It's New York City in 1981, and various twentysomethings are converging on a New Year's Eve party.

Starring: Ben Affleck, Casey Affleck, Dave Chappelle, Kate Hudson, Janeane Garofalo, Courtney Love, Jay Mohr, Nicole Ari Parker, Martha Plimpton, Christina Ricci ..
Directed by: Risa Bramon Garcia
Release date: 1999-02-26
30.

At First Sight

4.3
5.9/10 IMDB

A blind man has an operation to regain his sight at the urging of his girlfriend and must deal with the changes to his life.

Starring: Val Kilmer, Mira Sorvino, Kelly McGillis, Steven Weber, Bruce Davison, Nathan Lane, Ken Howard, Laura Kirk, Drena De Niro, Margo Winkler ..
Directed by: Irwin Winkler
Release date: 1999-01-15
31.

Three to Tango

4.2
6.0/10 IMDB

Oscar and Peter land a career-making opportunity when a Chicago tycoon chooses them to compete for the design of a cultural center. The tycoon mistakenly believes that Oscar is gay and has him spy on his mistress Amy. Oscar goes along with it and ends up falling in love with Amy.

Starring: Matthew Perry, Neve Campbell, Dylan McDermott, Oliver Platt, Cylk Cozart, John C. McGinley, Bob Balaban, Deborah Rush, Kelly Rowan, Rick Gomez ..
Directed by: Damon Santostefano
Release date: 1999-10-22
32.

Man of the Century

4.2
7.0/10 IMDB

Fantasy-comedy about a young man who lives as if it is 1928 or so, and his encounters with modern-day women and modern-day criminals.

Starring: Gibson Frazier, Cara Buono, Ian Edwards, Brian Davies, Susan Egan, Robert Lin, Yul Vazquez, Dwight Ewell, Brian Kite, David Margulies ..
Directed by: Adam Abraham
Release date: 1999-10-29
33.

Forces of Nature

4.1
5.5/10 IMDB

Ben Holmes, a professional book-jacket blurbologist, is trying to get to Savannah for his wedding. He just barely catches the last plane, but a seagull flies into the engine as the plane is taking off. All later flights are cancelled because of an approaching hurricane, so he is forced to hitch a ride in a Geo Metro with an attractive but eccentric woman named Sara.

Starring: Sandra Bullock, Ben Affleck, Maura Tierney, Steve Zahn, Blythe Danner, Ronny Cox, Michael Fairman, Richard Schiff, Athena Maria Bitzis, Afemo Omilami ..
Directed by: Bronwen Hughes
Release date: 1999-03-12
34.

Random Hearts

4.1
5.3/10 IMDB

After the death of their loved ones in a tragic plane crash, Sergeant Dutch Van Den Broeck and Congresswoman Kay Chandler find each other's keys in each other's loved ones' possessions and realize that the two were having an affair and they must figure out all the details.

Starring: Harrison Ford, Kristin Scott Thomas, Charles S. Dutton, Bonnie Hunt, Dennis Haysbert, Sydney Pollack, Richard Jenkins, Paul Guilfoyle, Susanna Thompson, Peter Coyote ..
Directed by: Sydney Pollack
Release date: 1999-10-08
35.

The Muse

4.0
5.7/10 IMDB

What happens when a screenwriter loses his edge, he turns to anyone he can for help...even if it's the mythical "Zeus's Daughter". And he's willing to pay, albeit reluctantly, whatever price it takes to satisfy this goddess, especially when her advice gets him going again on a sure-fire script. However, this is not the limit of her help, she also gets the writer's wife going on her own bakery enterprise, much to the chagrin of the screenwriter who has already had to make many personal sacrifices for his own help.

Starring: Albert Brooks, Sharon Stone, Andie MacDowell, Jeff Bridges, Cybill Shepherd, Jennifer Tilly, Monica Mikala, Jamie Alexis, Catherine MacNeal, Mark Feuerstein ..
Directed by: Albert Brooks
Release date: 1999-01-05
36.

A Season for Miracles

4.0
7.6/10 IMDB

A miracle occurs for a homeless family consisting of two wayward children and their protective aunt with the help of an angel. When a young woman's niece and nephew are threatened with foster care after her sister is hospitalized following yet another overdose, she flees with them until they land in the sleepy town of Bethlehem just before Christmas and a series of kindnesses and coincidences gives the trio a chance at happiness.

Starring: Carla Gugino, Kathy Baker, David Conrad, Laura Dern, Patty Duke, Lynn Redgrave, Mary Fogarty, Faith Prince, Evan Sabara, Mae Whitman ..
Directed by: Michael Pressman
Release date: 1999-12-12
37.

Trick

3.9
7.2/10 IMDB

Gabriel is a young, aspiring musical composer whose life seems stuck in the First Act. When his new musical number gets a critical reception, a theatre colleague, Perry, tells Gabriel that he needs to get a life before he can write about one – so he heads straight for his local gay bar.

Starring: Tori Spelling, Christian Campbell, John Paul Pitoc, Brad Beyer, Miss Coco Peru, Lorri Bagley, Steve Hayes, Kate Flannery, Nat DeWolf, Lacey Kohl ..
Directed by: Jim Fall
Release date: 1999-07-23
38.

Simply Irresistible

3.9
5.2/10 IMDB

After her mother's death, mediocre chef Amanda Shelton is having trouble attracting customers to her family's restaurant. While shopping for ingredients, she is given a magical crab by mysterious Gene O'Reilly. Afterward, Amanda's dishes suddenly become excellent, inducing strong emotional reactions in everyone who eats them. Tom Bartlett, who is preparing to open his own eatery, tries her cooking and falls in love.

Starring: Sarah Michelle Gellar, Sean Patrick Flanery, Dylan Baker, Patricia Clarkson, Lawrence Gilliard Jr., Christopher Durang, Betty Buckley, Olek Krupa, Amanda Peet, Alex Draper ..
Directed by: Mark Tarlov
Release date: 1999-02-05
Best Romance Movies of 1999 : George Lucas in Love
39.

George Lucas in Love

3.9
7.6/10 IMDB

1967 film student George Lucas has writer's block trying to finish his "Space Wheat" script, until a beautiful fellow student with a familiar hairstyle teaches him that the best stories are in plain sight.

Starring: Martin Hynes, Lisa Jakub, Jason Peck, Jeff Wiens, Patrick Kerr, Marilyn McIntyre ..
Directed by: Joe Nussbaum
Release date: 1999-09-18
Best Romance Movies of 1999 : Oklahoma!
40.

Oklahoma!

3.9
7.8/10 IMDB

Oklahoma! is a 1999 musical film directed by Trevor Nunn, choreographed by Susan Stroman, and starring Hugh Jackman as Curly McLain, Josefina Gabrielle as Laurey Williams, and Maureen Lipman as Aunt Eller. The production featured the entire 1998 London revival cast at the Royal National Theatre.

Starring: Hugh Jackman, Josefina Gabrielle, Shuler Hensley, Jimmy Johnston, Maureen Lipman, Peter Polycarpou, Vicki Simon, Stuart Milligan, David Shelmerdine, Rebecca Thornhill ..
Directed by: Trevor Nunn, Chris Hunt
Release date: 1999-09-26
41.

The Bachelor

3.9
5.0/10 IMDB

Jimmie is seeing his single friends get married one by one. He isn't too worried until his girlfriend Anne catches the bouquet at his friend Marco's wedding. Suddenly, his wild mustang days are numbered. He finally decides to propose to her, but he sticks his foot in his mouth and botches the proposal. Being insulted by the defeatist proposal, Anne leaves town on an assignment. After she's gone, he finds out that his recently-deceased grandfather's will stipulates that he gets nothing of a multi-million dollar fortune unless he's married by 6:05pm on his 30th birthday: tomorrow! Not being able to find Anne, Jimmie begins backtracking through his past girlfriends to find a wife.

Starring: Chris O'Donnell, Renée Zellweger, Artie Lange, Hal Holbrook, Ed Asner, James Cromwell, Marley Shelton, Peter Ustinov, Jennifer Esposito, Jason Aaron Baca ..
Directed by: Gary Sinyor
Release date: 1999-11-05
42.

The Wood

3.8
7.0/10 IMDB

In the panicky, uncertain hours before his wedding, a groom with prenuptial jitters and his two best friends reminisce about growing up together in the middle-class African-American neighborhood of Inglewood, California. Flashing back to the twenty-something trio's childhood exploits, the memories capture the mood and nostalgia of the '80s era.

Starring: Omar Epps, Richard T. Jones, Taye Diggs, Malinda Williams, Sean Nelson, Duane Finley, Trent Cameron, De'Aundre Bonds, Tamala Jones, Sanaa Lathan ..
Directed by: Rick Famuyiwa
Release date: 1999-07-16
43.

Smiling Fish & Goat On Fire

3.7
7.7/10 IMDB

Two brothers share a house in LA's Fairfax district: Tony's a feckless actor, Chris is an accountant. Both are in relationships on rocky ground. As these emotions swirl, Tony meets his US Postal Service letter carrier, a single mom named Kathy who's come to LA from Wyoming with her daughter, a budding actress. Chris meets Anna, an Italian beauty working in the States for a few months wrangling animals on movie sets. Chris also befriends Clive, an aging and crusty man whose longing for his recently-deceased wife is a portrait of true love. Can Clive's example help Chris sort out his love life, and can Tony grow up enough to see the possibilities with Kathy and her daughter?

Starring: Derick Martini, Amy Hathaway, Steven Martini, Wilda Taylor, Rena Riffel, Ion Overman, Christa Miller ..
Directed by: Kevin Jordan
Release date: 1999-09-16
44.

Twin Falls Idaho

3.7
7.1/10 IMDB

Francis and Blake Falls are Siamese twins who live in a neat little room in a rundown hotel. While sharing some organs, Blake is always fit and Francis is very sickly. Into their world comes a young lady, who turns their world upside down. She gets involved with Blake, and convinces the two to attend a Halloween party, where they can pass themselves off as wearing a costume. Eventually Francis becomes really ill, and they have to be separated. They then face the physical and mental strains that come from their proposed separation.

Starring: Mark Polish, Michael Polish, Michele Hicks, Jon Gries, Patrick Bauchau, Garrett Morris, Lesley Ann Warren, William Katt, Teresa Hill, Robert Beecher ..
Directed by: Michael Polish
Release date: 1999-07-30
45.

One Special Night

3.7
7.2/10 IMDB

Builder Robert is visiting his ailing wife in a nursing home and is having problems getting a taxi home due to an intense snow storm. One of the doctors, Katherine offers him a lift home however their car gets stuck and they have to spend the night in an empty cabin nearby. They talk and bond, but afterwards seem to have difficulty beginning a relationship.

Starring: James Garner, Julie Andrews, Patricia Charbonneau, Stacy Grant, Stewart Bick, Sam Stone ..
Directed by: Roger Young
Release date: 1999-11-28
46.

Jesus' Son

3.7
6.9/10 IMDB

A young man turns from drug addiction and petty crime to a life redeemed by a discovery of compassion.

Starring: Billy Crudup, Samantha Morton, Jack Black, Denis Leary, Dennis Hopper, Holly Hunter, Michael Shannon, John Ventimiglia, Will Patton, Miranda July ..
Directed by: Alison Maclean
Release date: 1999-09-05
Best Romance Movies of 1999 : The Magical Legend of the Leprechauns
47.

The Magical Legend of the Leprechauns

3.7
7.0/10 IMDB

American businessman Jack Woods rents a cottage on the enchanted Emerald Isle which is occupied by a family of leprechauns. Leprechaun Seamus Muldoon's son and son's friends crash the fairies' costume ball and Muldoon's son falls in love with fairy Princess Jessica. Their love re-ignites a feud between the leprechauns and the fairies, which escalates into a war. The Grand Banshee warns of terrible consequences and Jack Woods is chosen to make peace. Woods interrupts his own romance with an Irish beauty to help, and becomes involved in a strange and wonderful magical adventure.

Release date: 1999-11-07
48.

Solomon and Gaenor

3.6
6.8/10 IMDB

A young Jew in 1911 Wales tries to make his living by selling fabrics door to door, but to do so he must hide his nationality. On one of his sales he meets and falls in love with a demure young woman with a strong-willed father and a Jew-hating brother. The two fall in love and she becomes pregnant, but only then does she learn of his ethnic background. When anti-Jewish riots break out, the two are forced to flee and become separated.

Starring: Ioan Gruffudd, Nia Roberts, Sue Jones-Davies, William Thomas, Mark Lewis Jones, Maureen Lipman, David Horovitch, Steffan Rhodri ..
Directed by: Paul Morrison
Release date: 1999-04-30
49.

Onegin

3.6
6.8/10 IMDB

In the opulent St. Petersburg of the Empire period, Eugene Onegin is a jaded but dashing aristocrat - a man often lacking in empathy, who suffers from restlessness, melancholy and, finally, regret. Through his best friend Lensky, Onegin is introduced to the young Tatiana. A passionate and virtuous girl, she soon falls hopelessly under the spell of the aloof newcomer and professes her love for him

Starring: Ralph Fiennes, Liv Tyler, Toby Stephens, Lena Headey, Martin Donovan, Elizabeth Berrington, Alun Armstrong, Simon McBurney, Harriet Walter, Jason Watkins ..
Directed by: Martha Fiennes
Release date: 1999-12-22
Best Romance Movies of 1999 : Great Expectations
50.

Great Expectations

3.6
7.2/10 IMDB

A young boy called Pip stumbles upon a hunted criminal who threatens him and demands food. A few years later, Pip finds that he has a benefactor. Imagining that Miss Havisham, a rich lady whose adopted daughter Estella he loves, is the benefactor, Pip believes in a grand plan at the end of which he will be married to Estella. However, when the criminal from his childhood turns up one stormy night and reveals that he, Magwitch, is his benefactor, Pip finds his dreams crumbling. Although initially repulsed by his benefactor, Pip gradually becomes loyal to him and stays with him until his death.

Starring: Ioan Gruffudd, Justine Waddell, Charlotte Rampling, Laura Aikman, Nicholas Blane, Selina Cadell, Jo Cameron Brown, Tony Curran, Ian McDiarmid, Clive Russell ..
Directed by: Julian Jarrold
Release date: 1999-04-12

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