Julia, Julia & More Julia

In 1999, Marshall reunited Roberts and Gere (plus their Pretty Woman costar Hector Elizondo) in Runaway Bride. Roberts plays the not-quite-married Maggie who finds love with New York columnist Ike after he tracks her down while righting wrongs in the snarky piece he wrote about her. Though it failed to capture the magic of Pretty Woman, Runaway was a still a runaway hit at the box office.

Meanwhile, another soon-to-be Roberts costar launched lasting fame, this time from the other side of the pond.

Rare was the female moviegoer who, having purchased a ticket to 1994’s Four Weddings and a Funeral, didn’t fall for Hugh Grant’s charmingly rumpled Brit commitment-phobe Charles, who changes his mind something fierce when ballsy, beautiful American Carrie (Andie Macdowell) sashays into his life. And then out. And then in. Again and again and again. Bolstered by a stellar cast of wry comic talent, the scrappy, low-budget production stood out among its cookie-cutter romcom brethren, becoming an Oscar nominee, awards-season favorite and timeless rom-com hit.

Five years later, Four Weddings screenwriter Richard Curtis returned with Notting Hill (1999). Hugh Grant charmed once again as bumbly English bookstore owner William Thacker, who encounters Julia Roberts’ mega-movie-star Anna Scott when she wanders into his London shop. Longing for more than the glitz and artifice of Tinseltown, Anna falls for William until a series of unfortunate events sparks her apprehension and drives the pair apart. In true Hollywood fashion, Thacker is ultimately just a workaday boy standing in front of a really famous girl and asking her to love him once again.

Grant and Roberts each received a Golden Globe nomination for their work, and the film boasted the biggest opening for a romantic comedy ever, besting Roberts’ Best Friend’s Wedding, but soon ceding that record to her Runaway Bride.