The 1990s brought so many amazing rom-coms that people still watch over and over again. Characters’ internal struggles and daily lives were so compelling, and relationships started to take shape in nonconventional ways.
For the first time, people could tamper with their life situations using the Internet. They still had plenty of chance meetings and other in-person encounters, though. It’s interesting to remember who made a positive impact and who left something to be desired. As lovable as some 90s rom-com characters are, others are just terrible.
9. Peter (While You Were Sleeping)
While You Were Sleeping (1996) is a well-loved rom-com because of its complex story and its holiday-adjacent theme. Lucy (Sandra Bullock) spends most of the movie pining after Peter (Peter Gallagher), a man she doesn’t really know. After saving Peter’s life, Lucy masquerades as his fiancée while Peter remains unconscious. She starts to fall in love with Peter’s brother, Jack (Bill Pullman), while learning that Peter really isn’t such a nice guy. He’s actually pretty bad (and pretentious) for a character who spends most of the movie asleep.
8. Frank Navasky (You’ve Got Mail)
You’ve Got Mail (1998) is a favorite rom-com for people of many ages and backgrounds. The New York City tale shows that two people really can find love online. The problem is, both of those people are attached to others. Joe Fox (Tom Hanks) has a girlfriend named Patricia Eden (Parker Posey), and Kathleen Kelly (Meg Ryan) has a boyfriend named Frank Navasky (Greg Kinnear). Frank is a self-absorbed journalist who ends up being perfect for Patricia when Joe and Kathleen finally get together. Though Frank evidences small glimmers of caring for Kathleen, he talks about himself way too much and doesn’t pay enough attention to her.
7. Amber Mariens (Clueless)
Elisa Donovan is Amber Mariens in the 1995 Clueless film and its short-lived TV series. Amber is the resident snobby girl who is often a source of competition for Cher Horowitz (Alicia Silverstone) in the fashion and popularity departments. Amber isn’t the nicest person, but it can be funny when she sets herself up to be laughed at around Cher and Dionne (Stacey Dash).
6. Julianne Potter (My Best Friend’s Wedding)
Julianne Potter (Julia Roberts) is the lady everyone wants to root for in My Best Friend’s Wedding (1997). Fans of the movie feel for Julianne. Her best friend, Michael (Dermot Mulroney), is getting married. Julianne panics when she remembers that she and Michael made a pact that they would marry each other if they were still not married by the age of 28.
Michael’s fiancée, Kimberly Wallace (Cameron Diaz), might not be everyone’s favorite character, but she’s actually much better than Julianne, who spends most of the movie trying to sabotage her best friend’s wedding as audiences are, shockingly, supposed to root for her.
5. Sam Baldwin (Sleepless In Seattle)
Sleepless in Seattle (1993) is the Tom Hanks-Meg Ryan rom-com that doesn’t put the two together until the end of the movie. Hanks plays Sam Baldwin, a widow whose young son, Jonah (Ross Malinger), wants to see his dad remarry. Jonah calls into a radio program to match up his dad with someone, but Sam is incredibly difficult to work with. He is not sensitive enough to his son’s feelings and intentions, and Sam even yells at Jonah on occasion. The dad comes around when meets Annie Reed (Meg Ryan), but Sam Baldwin is not the most honorable leading man.
4. Meredith (The Parent Trap)
Meredith Blake (Elaine Hendrix) is the villain of The Parent Trap (1998). She is Nick Parker’s (Dennis Quaid) girlfriend and clearly dislikes children. Meredith aims to marry Nick for his money and ship Hallie (Lindsay Lohan) off to boarding school. After she meets Hallie’s twin, Annie (Lindsay Lohan), Meredith is even more resolved to oust the sisters, so she gives Nick an ultimatum. Thankfully, he chooses the twins and rekindles his romance with their mother, Elizabeth James (Natasha Richardson).
3. Clarice Kensington (It Takes Two)
It Takes Two (1995) has one of the best love stories out of any Mary-Kate and Ashley movie. The lookalikes meet by chance, but they come from completely different worlds. Mary-Kate is Amanda Lemmon, an orphan who has been through a lot. Ashley is Alyssa Calloway, a very wealthy girl whose mother has passed away. Amanda’s social worker, Diane (Kirstie Alley), would be perfect for Alyssa’s dad (Steve Guttenberg), but he’s engaged to a rotten socialite named Clarice Kensington (Jane Sibbett). Clarice couldn’t care less about Alyssa and would make a wretched stepmother. It’s hard to beat Meredith from The Parent Trap, but Clarice is the worst.
2. Mike Dexter (Can’t Hardly Wait)
Can’t Hardly Wait (1998) is the teen rom-com that brought numerous stars together for one big party. Mike Dexter (Peter Facinelli) is the jock who regrets dumping Amanda Beckett (Jennifer Love Hewitt). Mike is so conceited as he mocks kids who are less popular than him, and he’s the worst boyfriend of the whole bunch.
When Amanda doesn’t want to get back together with Mike, he rudely asks her, “You don’t want me to take you back?” Amanda’s response includes, “Take me back? Please.” Mike is effectively humiliated at the party, and rightfully so.
1. Philip Stuckey (Pretty Woman)
Pretty Woman (1990) is one of Julia Roberts’ most famous rom-coms, and she and Richard Gere have incredible chemistry in their respective roles as Vivian and Edward. Edward has a slimy lawyer named Philip Stuckey (Jason Alexander) who learns that Vivian is a sex worker and immediately begins to treat her poorly.
Philip is the worst 1990s rom-com character ever because he attempts to rape Vivian. Edward enters the scene quickly enough to help stop Philip. This kind of action qualifies Philip to be the worst character of any genre.