Should 've Been Us " is a song recorded by American singer and songwriter Tori Kelly for her debut studio album '' Unbreakable Smile '' ( 2015 ) . Written by Kelly with Ludvig Söderberg , Jakob Jerlström , Oscar Holter , Laleh Pourkarim , Alexander Kronlund and James Alan , and produced by The Struts and Holter , the song was sent to US mainstream radio as the second single from the album on June 2 , 2015 . A remix of the song featuring American singer Jeremih was released digitally in the United Kingdom on September 10 , 2015 , as Kelly 's first single there . " Should 've Been Us " is a pop song with influences of urban music . Lyrically , the song talks about an unrequited relationship , where she laments the failed romance and what it could have been like with her former lover . The song received generally favorable reviews from music critics , who commended it for being infectious and relatable . The song peaked at number 51 on the '' Billboard '' Hot 100 , becoming Kelly 's highest charting single to date in the United States . While promoting the song on a variety of television programs , as well as award shows , Kelly received high praise from critics , who positively highlighted her vocal performance , most notably at the 2015 MTV Video Music Awards
2015 MTV Video Music Awards
2015 MTV Video Music Awards
Should've Been Us