Amy Winehouse performs during the 46664 concert in celebration of Nelson Mandela's life at Hyde Park on June 27, 2008 in London. Sadness takes on different forms, from regret to depression to loss; ...

There are a lot of songs out there with upbeat melodies but also boast depressing or bittersweet lyrics. But, what about the other way around? This is a little rarer, but here are three songs that fit ...

Hip-hop has been cranking out living-it-up bangers for decades, but the average historian is (or should be) aware that dark thoughts aren't a foreign concept for the genre. After all, Grandmaster ...

A song often called one of the most depressing ever reached No. 2 on the Billboard Hot 100 50 years ago today, and its impact still lingers Eric Carmen's "All By Myself" peaked at No. 2 on Billboard ...

Few country songs stand the test of time like sad songs. The entire genre is built on songs that evoke strong emotions, including these three country songs from 1989, which are among the saddest ...

There are too many iconic David Bowie songs to list, but if there is one that stands out as the most heartbreaking one, that would be "Letter to Hermione." The song, from the legendary self-titled ...

Add Yahoo as a preferred source to see more of our stories on Google. Exactly 50 years ago today, on March 19, 1976, a song widely considered to be one of the most depressing to listen to was No. 2 on ...