1. Adventureland
   When Harry Met Sally
2. You're the Worst
   Master of None

"When Harry Met Sally" is a 1989 film with Billy Crystal and Meg Ryan as Harry and Sally. The movie was first written by Nora Ephron and directed by Rob Reiner and explores the idea of men and women being platonic friends through the interactions of the lead characters over 12 years.

1. Younger
   Scrooged
2. Knocked Up
   Bridesmaids

"Scrooged" is a modern adaptation of the 1843 novel "A Christmas Carol" starring Bill Murray as Frank Cross, a pessimistic and greedy television executive who is visited by the ghost of his mentor and the spirits of Christmas Past, Present, and Yet to Come.

1. Coming to America
   Definitely, Maybe
2. Insecure
   You're the Worst

"Coming to America" is a 1988 film that centers around Prince Akeem (Eddie Murphy) who moves to New York City with his sidekick Semmi (Arsenio Hall) to escape an arranged marriage and search for an independent wife who will love him despite his wealth.

1. Her
   Catastrophe
2. Sixteen Candles
   Knocked Up

"Sixteen Candles" is 1984 film starring Molly Ringwald, Michael Schoeffling, and Anthony Michael Hall. The film follows Samantha Baker, an angst-ridden teenager who deals with being overshadowed on her 16th birthday and pining for the affections of the older high school senior, Jake.

1. Pretty in Pink
   Jane the Virgin
2. Adventureland
   Drinking Buddies

"Pretty in Pink" is a 1986 film that stars Molly Ringwald as social outcast Andie whose only friends are her older manager Iona and her best friend Duckie (Jon Cryer), who has a crush on her. She eventually attracts the attention of popular boy Blane (Andrew McCarthy) and finds it difficult to date someone from a different social class.

1. Younger
   Bridesmaids
2. You're the Worst
   Tootsie

"Tootsie" is a 1982 film which centers around Michael Dorsey (Dustin Hoffman), a talented actor whose perfectionist tendencies makes him difficult to work with. Desperate for a job, he auditions for a female role as Dorothy Michael and gets the part, but complications arise when he develops feelings for his castmate Julie (Jessica Lange).

1. Definitely, Maybe
   Moonstruck
2. Warm Bodies
   Crazy, Stupid, Love

"Moonstruck" is a 1987 film about Italian-American widow Loretta (Cher) who is being pursued by Ronny (Nicolas Cage), the brother of her fiancé Johnny (Danny Aiello) while he is out of the country. Although she tries to resist his advances, she finds herself falling in love with him.

1. Crazy Ex-Girlfriend
   Roxanne
2. The Mindy Project
   The Proposal

"Roxanne" is a 1987 film, a modern adaptation of Edmond Rostand's 1897 play Cyrano de Bergerac. The film stars Hannah Daryl as the titular character Roxanne, and Steve Martin as C.D. Charlie Bales.

1. Master of None
   The Mindy Project
2. Warm Bodies
   About Last Night...

"About Last Night" is a romantic comedy-drama starring Rob Lowe and Demi Moore as Danny and Debbie, the former who enters a committed relationship for the first time. The film also stars James Belushi as Bernie Litko, Danny's best friend.

1. The Proposal
   500 Days of Summer
2. Hairspray
   Knocked Up

"Hairspray" is a 1988 dance comedy film starring Ricki Lake as Tracy Turnblad, an overnight teen who won a spot on her favorite dance show beating out the popular Amber von Tussle (Colleen Fitzpatrick) and drawing the attention of Amber' boyfriend, Lincoln Larkin (Michael St. Gerard).

1. Mannequin
   Adventureland
2. 500 Days of Summer
   The Proposal

"Mannequin" is a 1987 film starring Andrew McCarthy as a window designer whose previously designed mannequin comes to life and introduces herself as Emmy (Kim Cattrall). The two fall in love and create stunning window displays while fending off jealous competitors.

1. Knocked Up
   Bull Durham
2. Crazy Ex-Girlfriend
   Bridesmaids

"Bull Durham" is a 1988 romantic comedy that follows baseball groupie Annie Savoy (Suzanne Sarandon) who romances rookie pitcher Nuke (Tim Robbins) but finds herself falling for veteran catcher "Crash" Davis who was brought in to train Nuke for the major leagues.

1. Younger
   Risky Business
2. You're the Worst
   Drinking Buddies

"Risky Business" is a 1983 American film starring Tom Cruise as high school senior Joel Goodsen who hires a prostitute named Lana (Rebecca De Mornay) while his parents are away on a trip. He later turns the house into a brothel in a desperate attempt to raise money to pay Lana's bill and his father's wrecked Porsche.

1. Mystic Pizza
   Younger
2. Insecure
   Definitely, Maybe

Directed by Donald Petrie, "Mystic Pizza is an American coming-of-age film which revolves around the romantic lives of three teenagers Kat Araújo (Annabeth Gish), Daisy Araújo (Julia Roberts) and JoJo Barbosa (Lili Taylor) in the fictional town of Mystic, Connecticut.

1. Chewing Gum
   Jane the Virgin
2. Overboard
   Insecure

"Overboard" is a 1987 film starring Goldie Hawn as Joana Stayton, a snobbish and pampered woman who lost her memory after falling off her yacht. Her husband Grant (Edward Herman) sees this as a chance to get rid of her, while her former carpenter seizes the opportunity to get his revenge by claiming to be her husband.

1. Her
   Valley Girls
2. Obvious Child
   Catastrophe

Directed by Martha Coolidge, "Valley Girls" is a 1983 American film which follows Julie Rickman (Deborah Freeman) who is torn between choosing from her superficial friends and narcissistic boyfriend (Michael Bowen) or edgy Hollywood punk Randy (Nicolas Cage).

1. Chewing Gum
   Jane the Virgin
2. Some Kind of Wonderful
   Catastrophe

"Some Kind of Wonderful" is a teen drama film that revolves around high school outcast Keith (Eric Stoltz) who attempts to date popular girl Amanda (Lea Thompson) with the help of his tomboyish best friend Watts (Mary Stuart Masterson) who realizes she is in love with him.

1. Bridesmaids
   Obvious Child
2. Jane the Virgin
   Peggy Sue Got Married

"Peggy Sue Got Married" is a 1986 comedy-drama film starring Kathleen Turner as the titular character Peggy Sue Bodell, a married woman on the verge of divorce, who suddenly finds herself back at her senior year of high school, in the spring of 1960.

1. Catastrophe
   She's Gotta Have It
2. Insecure
   Chewing Gum

"She's Gotta Have It," written, edited and directed by Spike Lee, is a black-and-white comedy-drama film starting Tracy Camilla Johns as Nola Darling, a young, attractive woman from Brooklyn who cherishes her freedom by juggling three potential suitors.

1. Obvious Child
   Her
2. Blind Date
   Crazy Ex-Girlfriend

Directed by Blake Edwards, "Blind Date" is a 1987 film that follows bachelor Walter Davis (Bruce Willis) and Nadia Gates (Kim Basinger) whose seemingly average date spirals out of control throughout the night.

1. Adventureland
   Catastrophe
2. 500 Days of Summer
   Big

"Big" is a 1988 film centering 12-year-old Josh Baskin (David Moscow) who is transformed into a 30-year-old version of himself (Tom Hanks). Until he finds a way to change, Josh adjusts to adult life by working and soon becomes the romantic interest of his co-worker (Elizabeth Perkins).

1. Younger
   Crazy Ex-Girlfriend
2. Bridesmaids
   Can't Buy Me Love

"Can't Buy Me Love" is a coming-of-age romantic comedy film starring Patrick Dempsey as the nerdy Ronald Miller who gives popular cheerleader Cindy (Amanda Peterson) $1,000 to fix her mother's dress in exchange to pretend to be his girlfriend for a month.

1. Heathers
   Warm Bodies
2. Drinking Buddies
   The Proposal

"Heathers" is a 1988 black comedy about four popular teenagers, three of whom are named Heather. When clique member Veronica grows tired of the clique's cruel actions, she and newcomer J.D. accidentally kills her, masking her death as a suicide. However, J.D. goes overboard and starts killing students he doesn't like.

1. Insecure
   Her
2. Broadcast News
   Bridesmaids

"Broadcast News" is a 1987 film that centers around highly strung television news producer Jane Craig (Holly Hunter) who finds herself attracted to the arrogant anchorman Tom Grunick (William Hurt). Meanwhile, her best friend and reporter Aaron Altman (Albert Brooks) is secretly in love with her.

1. Working Girls
   Crazy Ex-Girlfriend
2. You're the Worst
   Master of None

"Working Girls" is a 1988 film starring Melanie Griffith as Tess McGill who gets back at her conniving boss Katharine Parker (Sigourney Weaver) who stole her business idea. When Katharine breaks her leg, Tess poses as her boss to pitch her business idea to an investment broker.

1. Obvious Child
   You're the Worst
2. Secret Admirer
   Jane the Virgin

"Secret Admirer" is a 1985 teen romantic comedy which follows Michael (C. Thomas Howell) who receives an anonymous love letter he believes is from the class beauty Deborah (Kelly Preston). However, his best friend Toni (Lori Loughlin) is secretly in love with him and is forced to watch from afar when he and Deborah begin a relationship.

1. Hannah and her Sisters
   Obvious Child
2. Catastrophe
   Bridesmaids

"Hannah and Her Sisters" is a 1986 Woody Allen film about three sisters Hannah, Lee, and Holly and the men they're involved with. Lee is having a secret affair with Hannah's husband Elliot, while Holly is tired of her failed careers and constantly borrowing money from Hannah.

1. Master of None
   Jane the Virgin
2. Say Anything
   The Mindy Project

"Say Anything" is 1989 American film written and directed by Cameron Crowe. The film stars John Cusack as Lloyd Dobler, an optimistic average student who captured the heart of valedictorian Diane Court (Ione Skye), much to the disapproval of her controlling father (John Mahoney).

1. The Proposal
   Her
2. Definitely, Maybe
   Look Who's Talking

"Look Who's Talking" is a 1989 film that chronicles Mollie Jensens' (Kirstie Alley) romantic ups and downs through the perspective of her talking newborn, Mikey. She develops a friendship with taxi driver James (John Travolta) who takes a liking to both her and Mikey.

1. Adventureland
   Weird Science
2. Warm Bodies
   Drinking Buddies

"Weird Science" is 1985 film starring Anthony Michael Hall and Ilan Mitchell-Smith as teenage misfits Gary and Wyatt. The pair designs their ideal woman on a computer but, following a freak electrical accident, the computer image is brought to life (Kelly LeBrock).

1. Her
   500 Days of Summer
2. Obvious Child
   Girls Just Want to Have Fun

"Girls Just Want to Have Fun" stars Sarah Jessica Parker as army brat Janey Glenn who competes in her favorite dance show when her father is transferred to Chicago. The film also stars Lee Montgomery, Helen Hunt, Morgan Woodward, Jonathan Silverman and Shannen Doherty.

1. Crazy, Stupid, Love
   Knocked Up
2. Arthur
   Jane the Virgin

"Arthur" is a 1981 film starring Dudley Moore as Arthur Bach, a wealthy and alcoholic Playboy millionaire who reluctantly agrees to an arranged marriage, but eventually falls for Linda Marolla (Liza Minnelli), a waitress from Queens.

1. Chewing Gum
   Romancing the Stone
2. The Mindy Project
   Insecure

"Romancing the Stone" is a 1984 romantic comedy-drama film starring Kathleen Turner as Joan Wilder, a lonely romance writer who must venture into the depths Colombian jungle to rescue her sister with the help of brash mercenary Jack Colton (Michael Douglas).

1. Younger
   The Princess Bride
2. 500 Days of Summer
   Master of None

"The Princess Bride" is a romantic comedy, fantasy adventure film depicting an enactment of a story being read to an unwell boy by his grandfather. The movie tells the story of Wesley (Cary Elwes) who must find his one true love Buttercup (Robin Wright) after a lengthy separation.

1. Master of None
   Her
2. Knocked Up
   The Purple Rose of Cairo

Written and directed by Woody Allen, "The Purple Rose of Cairo" is a romantic fantasy comedy film about picture show character Tom Baxter (Jeff Daniels) who steps out of the big screen and takes a liking to the clumsy and lonely waitress Cecilia (Mia Farrow).

1. Chewing Gum
   Tie Me Up, Tie Me Down
2. Catastrophe
   Definitely, Maybe

"Tie Me Up, Tie Me Down" is a Spanish dark romantic comedy starring Victoria Abril as Marina who falls in love with her captive Ricky (Antonio Banderas) who is determined to make her fall in love with him.

1. Catastrophe
   You're the Worst
2. Better Off Dead
   Crazy Ex-Girlfriend

"Better Off Dead" is a 1985 teen romantic comedy starring John Cusack as high school student Lane Myer who makes several bumbling attempts at suicide after his girlfriend Beth (Amanda Wyss) breaks up with him shortly before Christmas.

1. Baby Boom
   Jane the Virgin
2. Knocked Up
   Obvious Child

Directed by Charles Shyer, "Baby Boom" is a 1987 film starring Diane Keaton as J.C. Wiatt, an NYC businesswoman who, following the death of her long-lost cousin, becomes the caretaker of a six-month-old baby girl, which costs takes a toll on her relationship and job.

1. The Sure Thing
   The Mindy Project
2. Definitely, Maybe
   Crazy, Stupid, Love

"The Sure Thing" is a 1985 film starring John Cusack as Gib, a college freshman who carpools to California to meet up with a potential tryst. One of the passengers is the domineering Alison (Daphne Zuniga) who rejected his previous advances. As the two journey to California, they develop genuine feelings for each other.

1. Younger
   500 Days of Summer
2. The Mindy Project
   Mischief

Mischief, directed by Mel Damski, is a 1985 film about the introverted and clumsy Jonathan (Doug McKeon) who, with the help of extroverted womanizer Gene (Chris Nash), is determined to win the affections of the most popular girl in school Marilyn McCauley (Kelly Preston).