Best and Most Memorable
Film Kisses of All Time
in Cinematic History


1999


Best Movie Kisses of All-Time
Film Title/Year and Description of Kiss in Movie Scene
Screenshot

Cruel Intentions (1999)

'How to Kiss' Kiss

This dramatic film was a teenaged version of Dangerous Liaisons (1988), with the setting of modern-day New York City replacing the setting of France. It told of a complicated wager that involved seduction, revenge and manipulation, particularly evidenced in the "How to Kiss" scene between:

  • amoral, bitchy, deceitful teen-vamp Kathryn Merteuil (Sarah Michelle Geller) (this was one part of her wager with her step-brother Sebastian Valmont (Ryan Phillippe))
  • innocent, naive and virginal Cecile Caldwell (Selma Blair)

Kathryn demonstrated her manipulative intentions toward Cecile to destroy her reputation by teaching her how to slow- and wet-kiss in the park - as part of her scheme to provoke her to become promiscuous.

After a quick peck, Kathryn removed her sunglasses and proceeded to describe their next, more-involved kiss:

"OK, let's try it again only this time, I'm gonna stick my tongue in your mouth. And when I do that, I want you to massage my tongue with yours. And that's what first base is...Eyes closed!"

Following the tenderly-delivered wet French kiss, there was one strand of joined saliva stretched between them. Kathryn told Cecile: "Not bad," while Cecile assessed their lesbian smooch: "That was cool!"

[Note: Their kiss was spoofed in Not Another Teen Movie (2001).]



Entrapment (1999)

Age-Gap Kiss

Many reviewers and critics viewed the many kisses in this techno-thriller escapist caper flick (with numerous plot twists) as predatory between the two main characters. There was almost a forty year age difference between the two stars, who were engaged in a very uneasy partnership:

  • legendary coming-out-of-retirement master art thief Robert "Mac" MacDougal (69 year-old Sean Connery)
  • sexy undercover insurance investigator agent Virginia "Gin" Baker (30 year-old Catherine Zeta-Jones)

She schemed to 'entrap' him into performing a few large heists, including a multi-billion dollar New Year's Eve Millennium heist at the tall Patronas Towers in Kuala Lumpur, Malaysia.

At one pont in the film, when they were about to kiss, he reminded her:

Mac: "Young lady. You do realize I'm old enough to be your grandfather?"
Gin (correcting him): "My father."

By the film's end, she joined him for another kiss on the train platform and they disappeared together, planning to execute another job.





Eyes Wide Shut (1999)

Naked Mirror Kiss

The late Stanley Kubrick's last movie, about marriage and sexual jealousy, featured the highly sensationalized make-out scene before a dressing mirror table in the bedroom of a married couple, accompanied by Chris Isaak's "Baby Did a Bad Bad Thing":

  • Dr. William Harford (Tom Cruise)
  • wife Alice (real-life wife at the time Nicole Kidman)

Alice was seen naked from behind, but nude from the frontal view in the mirror. Bill approached from behind, looked at her, then himself in the reflection -- then began passionately kissing Alice on her neck, touched her breast, and then kissed her (as she took off her glasses and watched their reflection), before the brief scene faded to black.

Also, during the notorious, often-edited orgy sequence as the masked participants stood in a circle, a kiss was passed around.




Galaxy Quest (1999)

Alien Tentacled Kiss

In this comic parody of The Star Trek series in its tale of the stars of a cancelled sci-fi TV series that last aired in 1982, there was an unusual passionate make out scene between:

  • chief engineer Fred Kwan (Tony Shalhoub)
  • female Thermian alien Laliari (Missi Pyle) (in human form)

The kiss caused her to produce and expose purple tentacles that caressed and embraced him.

Guy Fleegman (Sam Rockwell) told them to "get a room" as they sank to the floor (and continued love-making off-screen), and he responded to what they were doing - beyond kissing: "Oh, that's not right!"




The Matrix (1999)

"The One" Reviving Kiss

In the Nebuchadnezzar hovercraft which was about to be assaulted by robotic Sentinels, Trinity (Carrie-Anne Moss) revived a dead Neo (Keanu Reeves) who had just been shot dead by Agent Smith (Hugo Weaving) within the Matrix.

She told him:

"Neo, I'm not afraid anymore. The Oracle told me that I would fall in love, and that that man, the man that I loved would be The One. So you see, you can't be dead. You can't be, because I love you. You hear me? I love you."

After kissing him, Neo's vital signs returned and she commanded him: "Now get up!"

After they were saved, they resumed kissing.



Never Been Kissed (1999)

Baseball Mound Finale Kiss

Drew Barrymore starred in this romantic comedy 'chick flick' as 25 year-old undercover Chicago Sun-Times copy editor Josie Geller, who was reporting on high-school life at her old school South Glen South High School (where she was formerly a geek) for a newspaper feature article.

During her investigative reporting, she fell in love with her English teacher, Mr. Sam Coulson (Michael Vartan) who couldn't act upon his affection for his underaged student and was trampled in the process.

In the film's conclusion, Sam read the revised article she had written in which she said she would stand on the pitcher's mound (for five minutes, registered on the countdown clock) in front of the assembled crowd at the start of the State Championship baseball game in Municipal Stadium, prior to the first pitch. If a "certain teacher" accepted her apology, she would kiss him - her "first real kiss."

After the clock countdown ended with Josie despondently left standing there alone, Sam finally appeared and approached the mound to passionately kiss her (to the tune of the Beach Boys singing "Don't Worry Baby"), and then apologized for being late.

Their smooch caused a kissing frenzy among various couples in the stands.




Notting Hill (1999)

Abrupt Kisses for Mismatched Lovers

This popular romantic comedy about mismatched lovers was set in London, and told of the circuituous route of the ultimately successful romance between:

  • American (Beverly Hills) movie superstar Anna Scott (Julia Roberts)
  • Notting Hill's recently-divorced travel bookshop owner William Thacker (Hugh Grant) of The Travel Book Co.

After a chance brief meeting in his bookshop, William literally bumped into her again on the street and spilled his container of orange juice. He offered to clean her up in his nearby apartment. As she left, he told her: "It was nice to meet you. Surreal, but nice." Almost immediately, she was back at the front door to retrieve her bookstore shopping bag, and before leaving a second time, she abruptly and spontaneously leaned forward and kissed him in the small front hall corridor before the door. William paused, and then apologized for his earlier rude comment about meeting her:

"I'm very sorry about the 'Surreal but nice' comment. Disaster."

Anna replied about how his unusual offer of food (apricots soaked in honey) from his kitchen's refrigerator was even worse: "That's OK, I thought the apricot and honey thing was the real low point."

While walking around Notting Hill later during one evening, they both climbed a five-foot fence and William, after struggling to clamber over the fence into a garden, said: "Now what in the world in this garden could make that ordeal worthwhile?" Anna leaned over and kissed him - their second, more romantic kiss. William paused and then said: "Nice garden."

Before she left London after filming wrapped, she came to his bookstore and said goodbye (with a gift) and an apology (for behaving badly), and asked if they could see each other again. He explained how there were major disparities between them, although she claimed she was "just a girl" seeking love:

William: "The thing is, with you, I'm in real danger. It seems like a perfect situation, apart from that foul temper of yours - but my relatively inexperienced heart would, I fear, not recover if I was once again cast aside, as I would absolutely expect to be. There are just too many pictures of you, too many, you know. You'd go and I'd be, uh, well, buggered, basically."
Anna: "That really is a real 'no,' isn't it?"
William: "I live in Notting Hill, you live in Beverly Hills. Everyone in the world knows who you are. My mother has trouble remembering my name."
Anna: "Fine, fine. Good decision. Good decision. The fame thing isn't really real, you know. And don't forget, I'm also just a girl, standing in front of a boy, asking him to love her."

After the confession, she gave him a quick kiss on the cheek before leaving the bookstore. Later, when William realized he had made the wrong decision about her, he raced to her (she was in the midst of a press conference before flying back to America that evening), and asked, in public, if she would reconsider her relationship with "Mr. Thacker" (who had been a "daft prick"). She answered affirmatively ("Yes, I believe I would"), and then said she would remain in London "indefinitely" - and the film concluded with their marriage.







The Sex Monster (1999)

Sex Monster Kisses

In this lightweight, teasing sex comedy farce, businessman Marty Barnes' (director/star Mike Binder) wife Laura Barnes (Mariel Hemingway) was encouraged to become involved in a threesome. She didn't realize that being introduced to experimental sex would lead to much greater Sapphic desire, making her an insatiable lesbian sex monster.

She came onto Diva (Missy Crider) by stroking her leg under an outdoor dinner table, and then apologized, although they ended up secretively lip-locking in the kitchen together:

Laura: "I'm so sorry. I really am. I'm sorry, Diva...I'm really sorry."
Diva: "You should be. I'm really not into women."
Laura: "Me neither." (Abruptly, they ravenously kissed each other)

To excuse her behavior to her husband, she rationalized her feelings for Diva when they were discovered together in bed: "Don't be upset...Why are you doing this? This, this is for you. This is for you. We are warming up for you" - although their later sexual threesome essentially ignored him.



Sleepy Hollow (1999)

An Unholy, Bloody Kiss

Director Tim Burton's stylized and Gothic R-rated version of the classic Washington Irving tale was set in late 18th century, post-colonial New York. The dazzling, visually-stunning film told about an awkward schoolteacher Ichabod Crane (Johnny Depp) who investigated a number of beheadings by a ruthless Hessian mercenary -- the Headless Horseman (Christopher Walken).

In the climactic scene, wicked Lady Van Tassel (Miranda Richardson), the stepmother of pretty Katrina Van Tassel (Christina Ricci), Crane's bewitched love interest, insanely explained how she had offered her soul to Satan in return for raising the Hessian from the grave for vengeance.

The Horseman - now re-headed after returning his skull to his neck and becoming flesh and blood again in an amazing transformation - took the insane Lady Van Tassel on horseback and kissed her. the Horseman's jagged-toothed face hungrily kissed her - when he withdrew, her lips were smeared with blood.

He then dove (horse and all) into the twisted Tree of the Dead in the Western Woods, his grave and entry point to the beyond, where they disappeared, although the living Lady Van Tassel was unable to pass through - her body was crushed and disintegrated as it entered. Only her hand remained outside the gnarled tree, with the index finger curled in a beckoning pose.




Sweet and Lowdown (1999)

"You Like Me?" Kisses

Writer/director Woody Allen's dramatic film told the story of self-absorbed and arrogant Depression-era American jazz guitarist Emmet Ray (Sean Penn).

After meeting and spending a "wonderful evening" together with mute laundress Hattie (Samantha Morton), he told her: "I don't need a genius to have a good time." He removed her cap and expected her to be shy and demure, but she ardently helped him by removing her outer garment. He expressed surprise at her quick aggressiveness:

"You know, uh, I'm a fast worker...Geez, you're not, uh, you're not much resistance. A lot of girls do on a first date."

When she began to tear off his clothes, he became startled:

"OK, yeah, hold on, hold it, time out, time out, just uh, I'm gettin' a little razzled at your pace. You like me? (She nodded) Really?"

He then mused: "Just expected more of a fight. It's like shootin' fish in a barrel" - noticing how eager she was to help him remove his clothes. The scene dissolved as she gave him a torrid kiss.

After making love and she was dressing, he asked:

"D'you like that? I knew you would. They say I'm a wonderful lover. You got a terrific body, you really do. Round, I like that. And I don't mean fat, you got some heft. Makes a fella feel like he's been someplace. Now get dressed! I'm tired. I gotta go to sleep. If I don't get my sleep, I'm cranky. I'm a little short this week or I'd give ya cab fare but I don't assume it's a long walk home. First time I had sex, seven years old..."

The World is Not Enough (1999)

A Neck-Breaking Torturous Kiss

In this 19th Bond film, the major 'Bond girl' villainess Elektra King (Sophie Marceau) used an ancient Spanish torture device - a bench-chair with a neck-breaking garrotte, to restrain and hold agent 007 James Bond (Pierce Brosnan), her former lover. She began to tighten the screw-bolt of the neck garrotte:

"Five more turns and your neck will break. I've always had a power over men."

She disclosed that she had mutilated her own right earlobe when past kidnapper and present co-conspirator Renard (Robert Carlyle) had refused to hurt her. And she argued that her father Sir Robert King (David Calder) had killed her ("He killed me the day he refused to pay my ransom"), and that was reason enough to kill him and fall in love with her captor Renard, due to the effects of the Stockholm Syndrome.

She then exclaimed how she was power-hungry to monopolize the oil empire inherited by her father:

"It is my oil. Mine, and my family's! It runs in my veins, thicker than blood. I'm going to redraw the map. And when I'm through, the whole world will know my name, my grandfather's name, the glory of my people!"

She was deluded and assured of her own success: "You understand? Nobody can resist me."

As Bond was on the verge of death, she straddled him. He begged her to reconsider and call off Renard's nuclear launch: "It's not too late. Eight million people need not die." She doubted that he would kill her, especially since she was someone that he had loved:

"You should have killed me when you had the chance. But you couldn't. Not me. Not a woman you've loved."

And she came close for a kiss. He struggled to tell her: "You meant nothing to me." She tightened the garrotte again, as he strained to say: "One last screw."




The World is Not Enough (1999)

A "Christmas" Kiss

The conclusion of this exciting action-packed Bond film was set in Istanbul, Turkey, where Bond was dallying with a second "Bond Girl':

  • agent 007 James Bond (Pierce Brosnan)
  • Dr. Christmas Jones (Denise Richards), a peculiarly named, buxom IDA (International Decommissioning Agency) nuclear physicist

They enjoyed champagne in fancy party clothes, and toasted themselves amidst fireworks and "Christmas" jokes (Bond: "I always wanted to have Christmas in Turkey"). She asked: "So isn't it time you unwrapped your present?"

They were spied upon enjoying intimacy in bed, by "R" (John Cleese) and M (Judi Dench) and other British Secret Service personnel in Scotland's castle. The couple was viewed via a thermal imaging camera (their bodies appeared orange in the image, and then turned redder as they had sex).

As Bond laid on top of Christmas and kissed her, he told her - with one of the cleverest, tongue-in-cheek Bondisms of all time:

"I was wrong about you...I thought Christmas only comes once a year."




Best and Most Memorable Film Kisses
(in chronological order by film title)
Introduction | 1896-1925 | 1926-1927 | 1928-1932 | 1933-1936 | 1937-1939 | 1940-1941
1942-1943 | 1944-1946 | 1947-1951 | 1952-1954 | 1955 - 1 | 1955 - 2 | 1956-1958 | 1959-1961
1962-1965 | 1966-1968 | 1969-1971 | 1972-1976 | 1977-1981 | 1982
1983-1984 | 1985-1986 | 1987 | 1988 | 1989-1990 | 1991 | 1992-1993 | 1994
1995 | 1996 | 1997 | 1998 | 1999 | 2000 | 2001 | 2002 | 2003 | 2004 | 2005 | 2006-2007 | 2008 | 2009-


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