Meester next appeared in "Like Sunday, Like Rain" directed by Frank Whaley, playing the girlfriend of Green Day's singer Billie Joe Armstrong, and "By the Gun", alongside Ben Barnes. She won the Best Actress Award for "Like Sunday, Like Rain" at the 2014 Williamsburg Independent Film Festival. She was the face of French brand Naf Naf's autumn/winter 2014 collection. On September 9, 2014, it was announced her debut album, "Heartstrings", would be released independently through her own label, Hotly Wanting, on October 28. With its style compared to ethereal singer-songwriters such as Tori Amos and Joni Mitchell, the nine-song LP was written by Meester and produced by Jeff Trott. The music video for the eponymous title track "Heartstrings" was released on October 29. In 2015, Meester embarked on a tour to support the album, which began on January 6 in Los Angeles, California and ended on March 2 in San Francisco, California. Later that year, she appeared in advertisements for the Malaysian fashion brand Jimmy Choo. Meester was one of the 100 celebrity narrators featured in the documentary "Unity", which had a limited theatrical release. In March 2016, she was cast in Fox's comedy series "Making History" as Deborah Revere, a colonial woman from 1775 and the daughter of American artisan Paul Revere. The series was cancelled after one season of nine episodes. Meester had a guest role on "The Last Man on Earth". In January 2018, Meester joined the cast of "Semper Fi", starring alongside Jai Courtney, Nat Wolff and Finn Wittrock, which was released in October 2019. Meester starred in ABC's "Single Parents" alongside Taran Killam, which premiered in September 2018 and was cancelled after two seasons. In 2019, Meester was a guest star in an episode of "The Orville" titled "Lasting Impressions" as Laura Huggins. Meester has participated in several charitable campaigns. In 2008, she was a spokesperson for Sunsilk's "Life Can't Wait" campaign, which aimed at motivating women to pursue their dreams. She also collaborated with Safe Horizon in 2009 to raise awareness about domestic violence. In 2015, Meester auctioned off fashion and accessories in a charity auction on eBay. The proceeds benefited Many Hopes, a charity organization that builds schools and homes for children in Kenya. Meester has been volunteering with the non-profit organization Feeding America since 2017.