4. Never Been Kissed: This 1999 romantic dramedy had Barrymore playing Josie Geller, a reporter, who goes undercover as a high school student for a story. Geller’s actual high school experience was horrific, but with the help of her brother, Rob, played by David Arquette, she slowly begins to fit in. Yet, she makes the mistake of falling for her English teacher, Sam Coulson, played by Alias’
Michael Vartan, which could blow her cover. Barrymore’s bubbly personality really gave Josie a genuine vibe as she bounced between her conflicting feelings for finishing her first real job assignment or having her first real relationship.