[2] After an early breakthrough with appearances in Mystic Pizza (1988) and Steel Magnolias (1989), Roberts established herself as a leading actress when she headlined the top-grossing romantic comedy Pretty Woman (1990).

[30] Following her first television appearance as a juvenile rape victim in the first season of the series Crime Story, with Dennis Farina, in the episode "The Survivor", broadcast on February 13, 1987, Roberts made her big screen debut in the dramedy Satisfaction (1988), alongside Liam Neeson and Justine Bateman, as a band member looking for a summer gig.

[31] Catapulting on her 1989 Academy Award nomination, Roberts gained further notice from worldwide audiences when she starred with Richard Gere in the Cinderella–Pygmalionesque story, Pretty Woman, in 1990, playing an assertive freelance hooker with a heart of gold.

[31] Roberts won the role after Michelle Pfeiffer, Molly Ringwald, Meg Ryan, Jennifer Jason Leigh, Karen Allen, and Daryl Hannah (her co-star in Steel Magnolias) turned it down.

[42] In 1991, Roberts played a battered wife attempting to begin a new life in Iowa in the thriller Sleeping with the Enemy, a winged, six-inch-tall tomboyish Tinkerbell in Steven Spielberg's fantasy film Hook and an outgoing yet cautious nurse in her second collaboration with director Joel Schumacher, the romance drama Dying Young.

[49][50][51] In 1996, she guest-starred in the second season of Friends (episode 13, "The One After the Superbowl"),[52] and appeared with Liam Neeson in the historical drama Michael Collins,[31] portraying Kitty Kiernan, the fiancée of the assassinated Irish revolutionary leader.

Mick LaSalle of San Francisco Chronicle stated: "When all else fails, there are still the stars to look at—Roberts, who actually manages to do some fine acting, and Gibson, whose likability must be a sturdy thing indeed.

[60] In 1998, Roberts appeared on the television series Sesame Street opposite the character Elmo, and starred in the drama Stepmom, alongside Susan Sarandon,[61] revolving around the complicated relationship between a terminally-ill mother and the future stepmother of her children.

[62] Roberts paired with Hugh Grant for Notting Hill (1999), portraying a famous actress who falls in love with a struggling book store owner.

CNN reviewer Paul Clinton called Roberts "the queen of the romantic comedy [whose] reign continues", and remarked: "Notting Hill stands alone as another funny and heartwarming story about love against all odds.

[69] Roberts was a guest star in "Empire", a Season 9 episode of the television series Law & Order, with regular cast member Benjamin Bratt, who at the time, was her boyfriend.

Though advertised as a typical romantic comedy star vehicle, the film does not focus solely on the actors' relationship and the two shared relatively little screen time together.

In Joe Roth's romantic comedy America's Sweethearts (2001), Roberts starred as the once-overweight sister and assistant of a Hollywood actress, along with Billy Crystal, John Cusack, and Catherine Zeta-Jones.

[78] Roberts received a record $25 million, the highest ever earned by an actress at that time, to portray a forward-thinking art history professor at Wellesley College in 1953, in Mike Newell's drama Mona Lisa Smile.

[80] In 2004, Roberts replaced Cate Blanchett in the role of an American photographer for Mike Nichols's film Closer, a romantic drama written by Patrick Marber, based on his 1997 play of the same name,[81] co-starring Jude Law, Natalie Portman and Clive Owen.

[86][87] She made her Broadway debut on April 19, 2006, as Nan in a revival of Richard Greenberg's 1997 play Three Days of Rain opposite Bradley Cooper and Paul Rudd.

[93] The independent drama Fireflies in the Garden, in which Roberts played a mother whose death sets the story in motion, was screened at the 2008 Berlin International Film Festival before being shown in European cinemas—it did not get a North American release until 2011.

Roberts played a CIA agent collaborating with another spy to carry out a complicated con, opposite Clive Owen, in the comic thriller Duplicity (2009).

[94] Despite mixed reviews and moderate box office returns,[95] critic A. O. Scott praised her performance: "Ms. Roberts has almost entirely left behind the coltish, America's-sweetheart mannerisms, except when she uses them strategically, to disarm or confuse.

In 2010, Roberts played a U.S. Army captain on a one-day leave, as part of a large ensemble cast, in the romantic comedy Valentine's Day, and starred as an author finding herself following a divorce in the film adaptation of Eat Pray Love.

[98][99] She appeared as the teacher of a middle-aged man returning to education in the romantic comedy Larry Crowne, opposite Tom Hanks, who also served as the director.

[103] Peter Travers of Rolling Stone felt that she tried "way too hard" in her role,[104] while Katey Rich of Cinema Blend observed that she "takes relish in her wicked [portrayal] but could have gone even further with it".

[117][118] She starred as a grieving mother opposite Nicole Kidman and Chiwetel Ejiofor in Secret in Their Eyes (2015), a remake of the 2009 Argentine film of the same name, both based on the novel La pregunta de sus ojos by author Eduardo Sacheri.

[120] Donald Clarke of Irish Times concluded that a "sound job" by the cast "can't quite shake the whiff of compromise that hangs around the project".

[121] In 2016, Roberts reunited with Garry Marshall and reportedly received a $3 million fee for a four-day shoot, playing an accomplished author who gave her child for adoption, in the romantic comedy Mother's Day, which had a lackluster critical and commercial response.

[122] Her next film release was Jodie Foster's thriller Money Monster, in which she starred as a television director, alongside George Clooney and Jack O'Connell.

[123] Sandra Hall of The Sydney Morning Herald stated: "It may be Hollywood melodrama but it's top of the range, giving Clooney and Roberts every opportunity to demonstrate the value of star power.

[133] The series, which premiered on Amazon Video in November 2018, garnered acclaim from critics, who concluded it was an "impressive small-screen debut" for Roberts that "balances its haunting mystery with a frenetic sensibility that grips and doesn't let go.

[137] She also played Martha Mitchell, a controversial figure throughout the Watergate scandal, in the political thriller television series Gaslit, based on the first season of the podcast Slow Burn by Leon Neyfakh.

[171] In September 2009, Swami Daram Dev of Ashram Hari Mandir in Pataudi, where Roberts was shooting Eat Pray Love, gave her children new names after Hindu gods: Lakshmi for Hazel, Ganesh for Phinnaeus and Krishna Balram for Henry.