"Heartaches" received renewed attention in the 2010s after several 1930s recordings of the song, including a version by Sid Phillips & his Melodians with Al Bowlly, were sampled in the Caretaker's album Everywhere at the End of Time.

[5] Weems' instrumental arrangement features a prominent whistling part by Elmo Tanner over what the bandleader described as a "corny sort-of half rhumba rhythm".

[1] Weems' career was put on hold in early 1942 when he and his entire band enlisted in the United States Merchant Marine to fight in the Second World War.

[7][8] In early 1947, Kurt Webster, a late-night disc jockey on WBT in Charlotte, North Carolina, a 50,000-watt station that reached across the East Coast, played Weems' 1938 version of "Heartaches".

[3] Webster enjoyed the tune and entered it into his regular rotation, leading to listeners frequently requesting it and "Heartaches" gaining national attention.

[11] In the United Kingdom, a recording of "Heartaches" by Vera Lynn was the most successful and the song impacted the sheet music chart from July to October 1947, peaking at number 10.

[16] In January 1948, Billboard listed the Ted Weems version of "Heartaches" as 1947's third biggest-selling record in the United States, behind The Harmonicats' "Peg O' My Heart" and Francis Craig's "Near You".

[27] From 2016 to 2019, English electronic musician Leyland James Kirby, also known as the Caretaker, sampled the Al Bowlly, Seger Ellis, and Guy Lombardo recordings of "Heartaches" for his final project, Everywhere at the End of Time; all three are used multiple times in the project and serve as one of its leitmotifs, with each subsequent appearance becoming more distorted and disfigured than the last, representing the gradual distortion and destruction of memory and other mental faculties brought about by dementia.

The complete edition of the project achieved viral popularity in October 2020 on TikTok as an online challenge, receiving notability from renowned publications such as The New York Times.