College graduates Sally Albright (Meg Ryan) and Harry Burns (Billy Crystal) debate whether men and women can strictly be platonic friends during a contentious car trip and the pair test their theories when they are reunited ten years later in this 1989 rom com.
In this 1990 film, Joe (Tom Hanks) is a hypochondriac who after learning he's dying decides to quit his job and accepts an offer to throw himself into a volcano on a tropical island. He didn't expect that along the way he would learn to live and fall in love with a woman named Patricia (Ryan).
Ryan takes on the role of Rita Boyle, a free-spirited graphic designer, who marries Peter Hoskins (Alec Baldwin), a conservative employee of a Chicago publishing house. At the wedding, she is approached by an elderly man named Julius (Sydney Walker) who asks for a kiss from her. When he does, their spirits switch until her new husband can see beyond the physical and Julius agrees to return his original body.
Ryan and Hanks reunite for this 1993 iconic rom com. Sleepless in Seattle tells the story of a man, Sam Baldwin (Hanks), who moved to Seattle with his son, Jonah, following the death of his wife. Jonah sets out to find a new partner for his father by calling into a radio program and Sam joins in the conversation. Annie Reed (Ryan) hears the show and falls for him. She then asks him to meet her at the Empire State Building on Valentine's Day.
The Connecticut native portrays Catherine Boyd who is the niece of physicist Albert Einstein. Despite being engaged to another man, a mechanic falls for her and gets the help of her uncle and his mischievous colleagues to make Boyd reciprocate his feelings.
The actress plays Kathleen Kelly, the owner of an independent bookstore The Shop Around the Corner in New York City, who starts to email with a mystery man only to find out that she has been corresponding with Joe Fox (Hanks), the man behind her competition, Fox Books.
When Kate (Ryan) discovers that her fiancé, Charlie (Timothy Hutton), has fallen for a Parisian woman, she decides to go to France to confront him. On the way, she is seated next to Luc (Kevin Kline), a charming crook who uses her to smuggle a stolen necklace. As the pair get to know each other, they begin to have feelings for each other and Kate must decide where her heart lies.
Things get complicated when astronomer Sam (Matthew Broderick) moves to New York City to stalk his ex (Kelly Preston) and her new boyfriend, Anton (Tchéky Karyo). He later meets, Maggie (Ryan) who is Anton's former girlfriend. The pair bond over their need to separate their exs and eventually fall for each other.
Ryan is Kate McKay, a modern day business executive, who falls in love with Leopold (Hugh Jackman), the third Duke of Albany from the late 1800s, when a rip in the fabric of time thrusts him into present day New York. An old-fashioned romance ensues between the duo.
Carter Webb (Adam Brody) is a successful writer who returns to his hometown of Detroit to help his grandmother (Olympia Dukakis) who is in failing health and begin work on his long-planned novel. While staying with his grandmother, he gets to know her neighbors—mom Sarah Hardwicke (Ryan) and her two daughters, Lucy (Kristen Stewart) and Paige (Makenzie Vega).
A struggling Hollywood producer cons a major studio into financing an action film following the adventures of 19th century British Prime Minister Benjamin Disraeli. He tries to get a studio executive (Ryan) to fall for him in the midst of making the film.
Ryan takes on the role of Louise, a high-powered Manhattan lawyer, who is shocked to discover her husband's (Hutton) affair with a much younger woman. Rather than letting him go, she decides to hold him captive until he commits to trying to make their marriage work.