[13] Bachelorette co-starred Kirsten Dunst, Lizzy Caplan, and Isla Fisher as three troubled women who reunite for the wedding of a friend played by Rebel Wilson, who was ridiculed in high school.

Television rights were acquired by NBC in 2013, to be executive-produced by Will Ferrell and Adam McKay; Krysten Ritter of the ABC series Don't Trust the B---- in Apartment 23 was set to both star and executive produce.

[15] Headland is the screenwriter of the 2014 remake of the film About Last Night, itself an adaptation of the 1974 David Mamet play Sexual Perversity in Chicago.

At the premier of the film, Headland said in an interview with The Wrap that her "elevator" pitch for the movie was, "Like When Harry Met Sally for assholes.

[22] Headland was hired by Netflix to direct the film Tell Me Everything, a thriller about marriage based on the young adult novel of the same name.

[28][29] It was revealed, in an May 2024 New York Times interview with Headland, that the show cost $180 million (for eight episodes) and took four years to make, with the interviewer, and New York Times reporter Brooks Barnes, arguing pleases fans of the original Star Wars and telling an "entirely new story...that showcases women and people of color.

[35][36] Others, such as Angela Watercutter of Wired, claimed that no review bombing was going on, but that people were only "expressing displeasure" for the series through audience scores.

"[38] As a playwright, Headland wrote the Seven Deadly Sins cycle: Cinephillia (lust), Bachelorette (gluttony), Assistance (greed), Surfer Girl (sloth), Reverb (wrath), The Accidental Blonde (envy), and Cult of Love (pride).

[44] Leslye Headland was brought up in a strict religious home and grew up watching the Marx Brothers and MGM musicals.

[45] Headland notes that Alfred Hitchcock's film Rear Window was the first time she saw the camera as a tool and realized what a director did.

[45] Later in life as she was completing her BFA at New York University, Headland notes the difficulty and dark time she faced due to the 9/11 attacks and names David Fincher's Fight Club as the reason she has a lifelong artistic need to make a joke about what is truly painful.