[[Berkas:Travel bookshop.jpg|250px|kanan|jmpl|Toko buku di Notthing Hill]]
Roberts berpasangan dengan [[Hugh Grant]] untukdalam film [[Notting Hill (film)|Notting Hill]] (1999),<ref>{{Citation|title=Notting Hill|url=http://www.imdb.com/title/tt0125439/|accessdate=2020-03-24}}</ref> ia memerankan seorang aktris terkenal yang jatuh cinta dengan seorang pemilik toko buku.<ref>{{Cite yangweb|url=https://variety.com/2019/vintage/news/notting-hill-richard-c-20th-anniversary-1203225966/|title=‘Notting kesulitanHill’ at 20: Why Julia Roberts Was the Only Choice to Play Anna|last=King|first=Susan|last2=King|first2=Susan|date=2019-05-28|website=Variety|language=en|access-date=2020-03-24}}</ref><ref>{{Cite web|url=https://www.eonline.com/ap/news/1040596/20-of-the-most-charming-secrets-about-notting-hill-you-could-imagine|title=20 Utterly Charming Secrets About Notting Hill|date=Tue May 28 03:00:00 PDT 2019|website=E! Online|language=en|access-date=2020-03-24}}</ref><ref>{{Cite web|url=https://people.com/movies/notting-hill-turns-20-surprising-facts/|title=Notting Hill Turns 20! Why Julia Roberts Almost Passed on Movie and More Surprising Facts|website=PEOPLE.com|language=en|access-date=2020-03-24}}</ref><ref>{{Cite web|url=https://primer.com.au/why-notting-hill-is-the-style-inspiration-we-all-need-2019/|title=Why Notting Hill Is The Perfect Fashion Inspo For 2019|date=2019-06-21|website=primer|language=en-US|access-date=2020-03-24}}</ref> Film ini mengalahkan [[Four Weddings and a Funeral]] sebagai hit terbesar Inggris dalam sejarah perfilman, dengan penghasilan setara dengan US AS$ 363 juta di seluruh dunia.<ref>{{Cite web|url=https://www.boxofficemojo.com/release/rl4016539137/|title=Notting Hill|website=Box Office Mojo|access-date=2020-03-22}}</ref> Sebagai contoh komedi romantis modern dalam budaya arus utama, film ini juga diterima dengan baik oleh para kritikus. CNN reviewer Paul Clinton menyebut Roberts "ratu komedi romantis", dan berkomentar: "Notting Hill sendiri merupakan kisah lucu dan mengharukan tentang cinta yang berhasil menghadapi segala rintangan."<ref>{{Cite web|url=http://edition.cnn.com/SHOWBIZ/Movies/9905/27/review.notting.hill/|title=CNN - Review: Julia, Hugh a perfect match for 'Notting Hill' - May 27, 1999|website=edition.cnn.com|access-date=2020-03-22}}</ref><ref>{{Citation|title=Notting Hill (1999)|url=https://www.rottentomatoes.com/m/notting_hill|accessdate=2020-03-24|language=en}}</ref>
Dia bersatu kembali dengan Richard Gere dan Garry Marshall, keduanya dari Pretty Woman, untuk memerankan seorang wanita yang telah meninggalkan tunangan di altar pada film Runaway Bride, yang dirilis pada 1999. Runaway Bride menerima ulasan yang umumnya beragam dari para kritikus, tetapi berhasil dengan sangat baik di box office, menghasilan AS$ 309,4 juta di seluruh dunia.<ref>{{Cite web|url=https://www.latimes.com/archives/la-xpm-1999-jul-30-ca-60883-story.html|title=It Looked Good on Paper|date=1999-07-30|website=Los Angeles Times|language=en-US|access-date=2020-03-22}}</ref><ref>{{Cite web|url=http://archive.vn/RKBmc|title=Review Roberts runs away with hearts in Runaway Bride - CNN|date=2013-01-19|website=archive.vn|access-date=2020-03-22}}</ref><ref>{{Cite web|url=https://www.rogerebert.com/reviews/runaway-bride-1999|title=Runaway Bride movie review & film summary (1999) {{!}} Roger Ebert|last=Ebert|first=Roger|website=www.rogerebert.com|language=en|access-date=2020-03-22}}</ref><ref>{{Cite news|title=FILM REVIEW; Pretty Woman Is Back, But Now She's Cautious|url=https://www.nytimes.com/1999/07/30/movies/film-review-pretty-woman-is-back-but-now-she-s-cautious.html|newspaper=The New York Times|date=1999-07-30|access-date=2020-03-22|issn=0362-4331|language=en-US|first=Janet|last=Maslin}}</ref><ref>{{Cite web|url=https://www.boxofficemojo.com/release/rl3295446529/|title=Runaway Bride|website=Box Office Mojo|access-date=2020-03-22}}</ref>
