In May 2017, during the Boston Calling Music Festival, Mac DeMarco delivered a notable performance characterized by both charm and adversity, as he faced technical issues including a malfunctioning guitar pedal and a broken acoustic guitar. At this point in his career, DeMarco had just released his highly acclaimed album "This Old Dog" in May 2017, which marked a significant evolution in his sound, showcasing a more introspective approach compared to his earlier work. This album explores themes of love and personal growth, reflected in both the music and his live persona. Additionally, his laid-back demeanor and unique engagement with the audience during this set underlined his reputation for creating a relatable and fun atmosphere, even in the face of challenges. The performance exemplified his ability to connect with fans, solidifying his position as a prominent figure in the indie pop scene during that time.