"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).

At the APRA Music Awards of 2019, the song was nominated for Rock Work of the Year.

[2] As of August 2020, the song is verified platinum for selling over 70,000 units.

Frontman David Le'aupepe said the song came about after struggling with a severe case of writer's block and questioning his place in the world.

The video was released on 8 August 2017 and shows Le'aupepe as a convict escaping in the early morning, as the sun rises through fields.