"The Deepest Sighs, the Frankest Shadows" is a song by Australian alternative rock band Gang of Youths, released in August 2017 as the fourth single from their second studio album Go Farther in Lightness (2017). The song peaked at number 93 on the ARIA Singles Chart, becoming the band's second top 100 single. Frontman David Le'aupepe said the song came about after struggling with a severe case of writer's block. On 27 January 2018, the song placed number five on the Triple J Hottest 100, 2017. At the APRA Music Awards of 2019, the song was nominated for Rock of the Year.