12 Songs to Make You Ugly-Cry

Some songs or other pieces of music just seem designed to tug at the ol’ heartstrings. To my knowledge, there is no technical term for this (at least musicologically – they might have something over in the psychology department, I don’t know). As an undergraduate music student, I was absolutely fascinated with these kinds of songs in particular. When I began writing this blog article, I sat down and started writing out songs that fit the bill for this. I came up with over 30 songs, just off the top of my head. If you would like to see them in a future blog post, please leave me a comment or send me an email.

We have all of music history and countless re-arrangements and covers to work with. A lot of times, taking an already emotional song and moving it into another genre or giving it a different interpretation will take an already good song and propel it above and beyond where it was. Sometimes, it just seems to BELONG to the original performer, and nobody else makes it work like they do, as if it fits them like a glove.

This type of song also tends to overlap with the ‘inspirational’ genre, so if you don’t see something here, it may turn up in a list more focused toward that type of song.

The following are presented in no particular order.


“Hurt” by Nine Inch Nails as performed by Johnny Cash


This is an interesting entry. “Hurt” was originally written and performed by Trent Reznor, the frontman for the band Nine Inch Nails. They are best described as an ‘Industrial Rock’ group – a loosely defined genre that fuses Rock Music with Industrial music (a very harsh and abrasive sounding genre). Before writing this, I’d only heard the Johnny Cash version, and decided to listen to the NIN version for comparison. Not my cup of tea, sure. It’s dynamics were terraced, and the only way the song built on itself was adding instrumentation. It starts out with just voice and guitar, then the drummer comes in, sounding like he is pounding on trash cans, and eventually – without warning – an overdriven electric guitar came in so loudly that I had to literally rip my headphones off my head.

The original was released by NIN in 1994, and it has that mid-90s sound to it.

In 2002, the late, great Johnny Cash covered the song. Well, ‘covered’ is putting it lightly. He completely reinterpreted it. The music video has been rated by some as the greatest ever produced. A clearly frail 71-year-old Cash presents the image of an elderly man – once widely popular – looking back at his 71 years – expressing his regrets. Almost as if to ask ‘What was all of this for? How did I end up here?’. He died a year later.



“Feel Like Going Home” by Charlie Rich


I feel like we’ve all identified at one point or another with what this song represents.

I’ve heard several ‘versions’ of this song. I feel like this – the ‘official’ version – is a bit too chipper in terms of tempo and instrumentation, but it still gets the job done.



“Angels” by Robbie Williams???? as performed by Josh Groban


There is a serious flag on the play as to who actually WROTE this song, but it seems to have been written by an Irish composer following a miscarriage by his partner, with the ‘angel’ in the song being his once-future daughter.

It was originally performed by British musician Robbie Williams and released in 1997. According to a poll conducted by the BBC as to which song Britons would like to have performed at their own funeral, this proved the most popular.


“Thank You” by Pentatonix


Pentatonix is known as an acapella group that mostly does covers. They do, however, have some originals, and will once in a great while use instruments.

I think that this song is especially emotional. Particularly for those of us who are terminally single.


“I’ll Be Seeing You” by Sammy Fain, as performed by Jimmy Durante


This is one of those great melancholy songs of the World War II era. Originally written in 1938, with the Great Depression in full swing and WW2 looming. It became widely popular, being performed by Billie Holiday, Bing Crosby, Frank Sinatra, and others.

Why the Jimmy Durante cover? Well, it’s a nostalgic song, ABOUT nostalgia, and I think that Durante’s staccato delivery, along with his gravelly voice and Lower East Side accent provides a nostalgic style that you just don’t hear anymore. It’s kind of the KFC Double-Down of music. Nostalgia sandwich with two pieces of Nostalgia as the bread.


“Blind Man in the Bleachers” by Kenny Starr


This song has kind of fallen into semi-obscurity. I don’t have much commentary to add except that I’m not crying … YOU’RE crying.


“Tom Traubert’s Blues” by Tom Waits


A list like this one wouldn’t be complete without a Tom Waits ballad. There are many to choose from, but this may be the best – certainly the most acclaimed. Waits is a brilliant lyricist, and he does a great job here of creating a sympathetic character who is in a hell of his own devising, while leaving it vague enough that the listener has to fill in the blanks of the whys and the wherefores of who this protagonist is and why they are in this situation.

I’ve heard no fewer than three contradicting stories about what inspired Tom Waits to write this song, and I’m not convinced that any of them represents the complete truth.


“Can’t Help Falling in Love” as performed by Haley Reinhart ft. Casey Abrams


Haley Reinhart isn’t a household name, but she really should be, and her style is perfect for this song. This performance also features Casey Abrams on the piano, and notice what he is doing. Listening to Haley, watching for her to cue him as to when to continue on, and keeping his accompaniment just loud enough and using just enough complexity to support her performance, without taking liberties or trying to steal a bit of the spotlight. I can tell you from experience that great accompanist can take a good performance and make it great.


“This Nearly Was Mine” from South Pacific by Rodgers and Hammerstein, as performed by Brian Stokes Mitchell


To be honest with you, I’ve never been nearly as into musical theatre as my colleagues from choir teacher college, and I’m not really up on the latest shows. Those cost a fair chunk of time and money to see, and as I’ve mentioned before, I ain’t rich.

I do – however – know a bit about the older Rodgers and Hammerstein musicals. R&H tend not to get much attention these days, particularly compared to your ‘Rent’s and ‘Mama Mia’s and ‘Dear Evan Hansen’s and whatever just premiered on Broadway last week. I feel like the old musicals are considered to be such big blocks of cheese that you say ‘Hey, kids, Sit down and watch this VHS copy of Robert Wise’s 3-hour-long film version of ‘The Sound of Music’, k?’

In actuality, the old musicals manage to cover some very weighty topics …. while, you know, still having plenty of cheese.

Brian Stokes Mitchell manages to imbue this song about rejected/unrequited love with all of the gravitas it deserves, and then some.


“In the Real World” by Roy Orbison


In the real world
There are things that we can’t change
And endings come to us
In ways that we can’t rearrange

I think that one of the cruelest things we do to children is teach them – through all sorts of stories and folklore and Disney-type movies – that everybody gets their ‘happily ever after’. For most people, the life that they dreamed of when young fails to materialize in some way – maybe you don’t get the career, or the family, or the income, or the health, or achievements that you always dreamed of. In some cases, you don’t get any of those things at all. Sometimes you get all of them. As much as we like to think that we can shape our own destiny, It’s really 90% in the cards you’re dealt, and maybe 10% in what you do with them. As John Green wrote in his blockbuster YA novel The Fault in our Stars “Apparently, The world is not a wish-granting factory”.


“We’ll Meet Again” as performed by Dame Vera Lynn


Another great piece of wartime nostalgia, performed by the late great English vocalist, Dame Vera Lynn.


“He Stopped Loving Her Today” by George Jones


I know that I said these were in no particular order, but I did save this for last. Presented without comment.

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