Three years before he died, Hank Williams poured out all the pain from his failing marriage to his wife Audrey Sheppard into this masterpiece. Williams wrote hundreds of songs and scored many huge hits during his brief life, but this is one of the few you still hear all the time, all these decades later. That's probably because the message is so universal and his raw pain is impossible to ignore. It's since been covered by everybody from Elvis Presley to Johnny Cash to Yo La Tengo. 

Like many songs on this list, the 1994 Alice in Chains classic "Nutshell" took on a new meaning after the singer Layne Staley died tragically at a young age. When you listen to this song today, it's impossible not to think about his death, and lines like "I'd feel better dead" are positively chilling. This ballad was never a single and it sounds unlike their famous works from this period, but it touched a nerve with fans and remains one of their most popular tunes. Alice in Chains play it at most every show, and it's a wonderful tribute to the spirit and resolve of Staley. 

Injured war vets and heroin addicts are both great subjects for sad songs. John Prine managed a rare feat in 1971 when he combined them both in his hit song "Sam Stone." It's about a Vietnam War veteran returning home with a taste for smack. He's eventually reduced to robbery to feed his habit. The chorus is one of the saddest in pop history: "There's a hole in daddy's arm/ Where all the money goes/ Jesus Christ died for nothing/ I suppose." He dies at the end after "popping his last balloon" in a "room that smells just like death." 

Pearl Jam were still gigging in Seattle clubs as Mookie Blaylock when they debuted "Black," a sad tale of lost love. Guitarist Stone Gossard cut the demo before he'd even met Eddie Vedder, who later wrote the lyrics while he traveled to Seattle to meet the band. They were thoroughly impressed by his work and offered him the job. They have played the song about 480 times, and it always gets the crowd to sing "I know someday you'll have a beautiful life/ I know you'll be a star in somebody else's sky" at the top of their lungs. 

There are a lot of truly sad country songs, but George Jones' 1980 hit "He Stopped Loving Her Today" stands above almost all of them. It came out years after Jones' commercial peak and he even thought it was too sappy, but he recorded it anyway and it shot to the top of the country charts. Simply put, it's about a guy whose friend holds onto his lost love until the day he dies. She attends his funeral, even though he spent decades pining for her in vain. Other singers would have had difficulty pulling it off, but Jones managed to convey the song without a hint of sap. Alan Jackson sang the song at his funeral earlier this year.

There's a lot of competition for the title of saddest Nirvana song, but "Something in the Way" is a very strong candidate. The slow ballad, which recounts Kurt Cobain's supposed time sleeping under a bridge in Aberdeen, Washington wraps up Nevermind. He recorded the track solo and acoustic, and the rest of the band later cut their parts. Rarely has Kurt sounded this vulnerable and raw. The version on MTV Unplugged is even more intense. 

AM radio was full of tearjerker songs in the 1970s, but Harry Chapin's 1974 hit "Cat's in the Cradle" is the king of them all. As everyone who ever attended summer camp knows, it's about a father who is too busy to spend time with his son. At the end, the grown-up son is too busy for his elderly father. It began as a poem by Chapin's wife, Sandy; her first husband's father was a New York politician and they had a strained relationship. Chapin died in a car accident in 1981 and he never got to see his own children grown up, making the song somehow even sadder. 

There weren't a lot of R.E.M. songs with a straightforward message before "Everybody Hurts." "The One I Love" is an anti-love song, "Gardening at Night" is just confusing and we're still trying to figure out "Losing My Religion." But there's no mistaking the message of "Everybody Hurts" – it's right there in the title. The iconic video showing depressed people in a traffic jam was filmed in San Antonio, Texas. MTV played it all the time in 1993, making this one of R.E.M.'s most well-known songs. 

Here's a line straight from the Associated Press' recent review of a Nine Inch Nails concert: "NIN closed the night with a slow and smoky cover of Johnny Cash's 'Hurt.'" The Internet had a field day making fun of the wire service for the glaring error, and the article has since been removed from the site, but it's easy to understand how such a thing happened; Johnny Cash's 2002 cover has basically supplanted the original in the hearts of the public. Cash was a year away from dying when he cut the song, and he turned the tale of heroin abuse into a look back on his life while barely changing any of the lyrics. June Carter Cash appeared in the video just three months before she died. Without any dispute, it was Cash's final masterpiece and the perfect epitaph. When you hear Trent Reznor singing it today, it's nearly impossible to not think about Johnny Cash. 

Eric Clapton's son Conor was just four years old when he fell to his death from the 53th floor of a New York building in 1991. Not long after the tragedy, Clapton and songwriter Will Jennings penned "Tears in Heaven" as a tribute to the child. They never imagined it would become a huge hit, but within months, it was Number Two on the Hot 100 and swept the Grammys. The song first appeared on the soundtrack to the widely forgotten Jason Patric movie Rush, but the version most people remember comes from Clapton's 1992 Unplugged special. By 2004, Clapton could no longer bear to perform the song at his shows and he dropped it; it returned earlier this year.