Bob Seger co-wrote 'Heartache Tonight' with Glenn Frey for the Eagles' 1979 album The Long Run, drawing inspiration from Sam Cooke records they had been listening to together. Despite the song's popularity and fan interest in a Seger version, the accomplished rock songwriter chose not to record it himself because of a vocal challenge that would impact its performance viability.

The primary obstacle was the song's range—it sits at the upper limits of Seger's vocal capabilities, requiring him to strain his voice to deliver the highest notes. Recognizing this limitation, Seger decided against recording his own rendition, aware that performing it repeatedly on tour would risk vocal damage. In interviews, he acknowledged that while he could occasionally nail the track, subjecting himself to singing it night after night across different venues would be unsustainable.