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; ...

Ryan is a lifestyle and culture journalist born and raised in the Philippines. He primarily covers film, television, music, and all things pop culture. Beyond writing, you can find him buried in ...

The Beatles wrote 20 No. 1 hits, but their most heartbreaking song never became a chart-topping single from the landmark 1967 ...

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 ...

Country music covers a wide range of topics with lyrics that speak to the best of times and the hardest of times. While there are plenty of songs about love, drinking, dancing, and living life to the ...

Olivia Rodrigo's new album 'You Seem Pretty Sad for a Girl So in Love' has arrived. Here's all 13 tracks ranked.

As the title suggests, “You Seem Pretty Sad” takes listeners through the lifespan of a relationship, from giddy beginnings full of butterflies (“Drop Dead,” “Stupid Song”) to the first thoughts of ...