How To Make Friends And Family Cry On Game Night: The Musical Sad-Off


Sad Boy How To Make Friends And Family Cry On Game Night: The Musical Sad Off

C’mon, kids! It’s Family Game Night!

This past Saturday night was a relatively quiet one at our home. But then the iPod pulled a sad song up from its depths, flooding our household with strains of abject woe. After a knowing glance from my 13 year-old daughter, it was ON: A Musical Sad-off.

It’s a favorite game between my daughter and I (we’re kinda sadistic that way). We used to play just your run-of-the-mill Storytelling Sad-Offs, but after the mini-household breakdown I caused with my fanciful tale of a swollen, elderly woman wearing a velour robe and faded rhinestone turban rummaging through clearance chocolate bins in Walmart the week after Christmas, we decided to stick with just the musical variety.

Why not try a Musical Sad-Off  this week for Family Game Night? There are only a few simple rules:

  1. No Leonard Cohen or Neil Young. Too easy.
  2. The entire song must be played to ensure that the full sadness quotient is realized.
  3. Anything with harmonica gets bonus points.
  4. Tap-outs MUST be respected.

Here are some of my personal favorite Sad-Off staples to get you started:

Yellow Ledbetter – Pearl Jam (1992)

I’d love to tell you what this song is about, but I have no idea. Eddie Vedder could tell me he took care of my massive student loan, is paying for my daughter’s braces and filled my gas tank, and I’d probably still cry. There’s something in his voice that just doesn’t leave room for joy. The only thing I can glean from “Yellow Ledbetter” is something about coming home in “a box or a bag,” and I’m pretty sure he’s not talking about crispy take-out fried chicken.

Ho Hey – The Lumineers (2012)

He’s been trying to do it right. He’s been living a lonely life. And you’re STILL gonna go off with that other dude? He doesn’t think you’re right for him. You belong with him!  He belongs with you! WHY AREN’T YOU LISTENING?

The River – Bruce Springsteen (1980)

Ah, teen love. We’ve all been there, right? Some of us more than others…ahem. And what do teens in love do? They go driving in cars. They go down to the river. They get pregnant, conceive a baby, get married by a sour-faced judge, get shitty blue collar jobs and die unfulfilled. YAY FOR TEEN LOVE!

Springsteen brings it home in “The River.” Parents of teens, forget everything you had planned for “the talk” about birth control. Simply play “The River” on low volume all night while your teen sleeps. It’ll become so engraved in their subconscious that they won’t be able to get it on in spite of their raging boners.

Also, they’ll be able to play harmonica. Win/win.

I Can’t Make You Love Me – Bonnie Raitt (1991)

If Bonnie Raitt can’t make someone love her, I guess we’re all fucked.

Wreck of the Edmund Fitzgerald – Gordon Lightfoot (1976)

When American Great Lakes freighter the SS Edmund Fitzgerald sank in stormy waters on Lake Superior in November 1975, resulting in the deaths of 29 men, no one sat up and said, “Hey guys, this is gonna make a great song!”

Except that someone did, and it is indeed awesome. Gordon Lightfoot’s haunting rendition of the men and their final moments before becoming doomed to a frozen watery grave is a must for any musical sad-off:

“And all that remains is the faces and the names/of the wives and the sons and the daughters.”

Good times, good times.

Space Oddity – David Bowie (1969)

From the time Ground Control says, “Your circuits dead, is there something wrong?” we knew. WE KNEW. Major Tom is not coming home, he’s not going to be able to tell his wife he loves her, and he’s definitely not going to be able to tell the paper whose shirts he wears.

This song is extra sad because it’s space. You get lost up there? You’re done. It’s hopeless. Earthly problems like an unplanned teen pregnancy and unrequited love aren’t looking so bad now, are they?

Sam Stone – John Prine (1971)

If you’re not acquainted with John Prine, become so immediately. Warning: do not attempt your first listen unsupervised, post break-up, or within 10 miles of a liquor store. He’s that good at making you feel bad.  Prine has long been underrated as a musician but the fact is the man writes a song and picks a guitar like no one else. (DO NOT argue this with me. I’m small, but I’m mean, and when it comes to Prine, even my kids won’t cross me and they are not afraid of anything.)

I chose “Sam Stone” as the Prine selection for this list but any one of these of his would work also:

Angel from Montgomerybonus points for version by Bonnie Raitt: “If dreams were lightning, and thunder were desire/This old house woulda burnt down a long time ago.”

Hello in There: “We lost Davey in the Korean war, and I still don’t know what for, Don’t matter anymore.”

Christmas in Prison: “It was Christmas in prison, and the food was real good, We had turkey and pistols carved out of wood.”

I swear to God these are real songs.

So, the next time you’re gathered around a formal dinner table with extended family, and there’s a lull in the conversation, start a Musical Sad-Off! Make that bitch sister-in-law cry for the first time in her frigid, tight-assed life. It’ll be fun!

What would you add to the list? C’mon, make me cry, I dare ya! Leave your addition(s) in comments!

source, source, source, source

About Jeni Marinucci

Jeni is a freelance writer with two children, countless dead hamsters, and a questionable home-haircut. She blogs at Highly Irritable and can be found on Twitter at @highlyirritable



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  • Lisa Rae @ smacksy

    Challenge accepted. Get out your Kleenex.
    “My Mom” by Chocolate Genius
    http://www.youtube.com/watch?v=ESQHGVlnDk4&feature=share&list=AL94UKMTqg-9C_24nE5IVtrCsH29dFCEsd

    • http://twitter.com/highlyirritable Jeni M

      Oh, Lisa. WHY ARE YOU SO CRUEL?

  • Jody

    Sappiest country song ever. You know how it’s gonna end. But it doesn’t matter. When it happens at 3:09, you’re a goner. http://youtu.be/Rf_UV0TAjM8

    • http://twitter.com/highlyirritable Jeni M

      Oh, sweet Jesus. Heed her warning, people! Jody, I almost made a “NO country music” provision for exactly this reason – the songs are too damn sad!

  • nyoprinces

    I can up-sad your sad. The first time I heard “Ho Hey,” I was driving to the hospital. I was on my way to visit my daughter, who was still in the NICU even though her twin brother had been released, so I was having to leave one of my babies at home while I visited the other in her now-half-empty twin-sized room and begged her to gain enough weight to come home. As I pulled into the hospital complex, I heard the chorus for the first time – “I belong with you, you belong with me, you’re my sweetheart.” I sang that chorus to her every night until she came home.

    On the happy side, she and her brother are now happy, healthy, perfect 9-month-olds.

    • http://twitter.com/highlyirritable Jeni M

      You are a Sad Master. I bow to your sad, because it is the best kind – the kind with not only one, but *two* happy endings!
      P.S. Are not 9mo babies just the BEST?

      • nyoprinces

        They are TOTALLY the best. I’ve never had so much fun in my life.

        • http://twitter.com/highlyirritable Jeni M

          This here comment just erased, like, half the sad I’ver accumulated from these songs.

    • http://www.facebook.com/traceygaughranperez Tracey Gaughran-Perez

      Just reading this comment made me tear up. Jesus. You win ALL OF THE THINGS.

  • http://www.facebook.com/amy.l.holiday Amy Leonard Holiday

    Hmm, the Country genre seems too easy, but “He Stopped Loving Her Today” by George Jones is pretty fookin sad

    http://www.youtube.com/watch?v=1R2F9f2Cl6Y

    Also, “Two out of Three Ain’t Bad” by Meatloaf

    http://www.youtube.com/watch?v=q8JA9Qs2Mho

    And The Carpenters version of “Superstar” gets extra sad points because of skeletal Karen Carpenter. Heartbreaking.

    http://www.youtube.com/watch?v=F9Nm_0pC4FM

    I’m old as hell.

    • http://twitter.com/highlyirritable Jeni M

      Ouch. I thought about including the George Jones one, but couldn’t bring myself to do it out of concern for others. But hey; you went there. I can respect that. ;)

    • http://twitter.com/ryenerman ryenerman

      Oh God George Jones – just thinking about that is making me weepy at the damned office.

  • http://www.facebook.com/people/Amie-Kitchen/540433316 Amie Kitchen

    Pearl Jam gets my vote, though my biggest sad-off song from them is Just Breathe. I have to run for the kleenex every time I listen to this song.

    https://www.youtube.com/watch?v=aePWkeDxRjE

    • http://twitter.com/highlyirritable Jeni M

      …and now I”m crying for reals. THANKS, AMIE.

  • http://www.facebook.com/people/Amie-Kitchen/540433316 Amie Kitchen

    Oh, and one more, from Gotye, turns me into a weeper.

    https://www.youtube.com/watch?v=le34ygtODfI

  • http://www.facebook.com/traceygaughranperez Tracey Gaughran-Perez

    This one always turns the waterworks to ELEVEN for me: http://www.youtube.com/watch?v=SDsxkQk6DWw

    • http://www.facebook.com/traceygaughranperez Tracey Gaughran-Perez

      Actually, scratch that – I prefer this version: http://www.youtube.com/watch?v=sQLfPwAxUPQ

      • http://twitter.com/highlyirritable Jeni M

        My playlist just got one song longer. This was an unknown to me; thank you! (I think?)

        • http://www.facebook.com/traceygaughranperez Tracey Gaughran-Perez

          The lyrics to that read like pure poetry:

          Once I wanted to be the greatest
          No wind or waterfall could stall me
          And then came the rush of the flood
          The stars at night turned deep to dust

          Melt me down into big black armor
          Leave no trace of grace just in your honor
          Lower me down to culprit south
          Make ‘em wash a space in town

          For the lead and the dregs of my bed
          I’ve been sleeping
          Lower me down, pin me in
          Secure the grounds for the later parade

          Once I wanted to be the greatest
          Two fists of solid rock
          With brains that could explain
          Any feeling

          Lower me down, pin me in
          Secure the grounds
          For the lead and the dregs of my bed
          I’ve been sleeping for the later parade

          Once I wanted to be the greatest
          No wind or water fall could stall me
          And then came the rush of the flood
          The stars at night turned deep to dust

          I have no idea what all of it means, logically, but I do know it makes me cry like a goddamn baby.

          • http://www.facebook.com/traceygaughranperez Tracey Gaughran-Perez

            (I’m pretty sure it has something to do with Hurricane Katrina, and death, and Muhammed Ali…. but beautifully mashed up and poetically rendered.)

  • diamondcait

    “Sand and Water” by Beth Carpenter, or “Scarlet Tide” by Alison Krauss will bring on the tears anytime. Almost all John Prine will qualify. But I would disqualify the Edmusd Fitzgerald for its earworm properties.

    • Judy P

      Oh my gosh, I LOVE Sand and Water, although that is one I can listen to while driving. None of the ones I linked are allowed to get past the opening notes if I’m driving. And even the opening notes of “Oklahoma” get me doing the yoga breathing…

      • http://twitter.com/highlyirritable Jeni M

        Yes! I LOVE the ones that catch you in the throat with just the opening notes. Like ripping open a scab, or some such.

    • http://twitter.com/highlyirritable Jeni M

      Have you ever seen John Prine live? He’s such a happy guy, and the energy at his concerts is so mellow.

  • Judy P

    I am the queen of the sad song. I had to create a playlist on my iPod for melancholy days because the overall playlist contains so many cry-bombs. Pretty much all my submissions are gonna slay the parents here. Apologies in advance.

    “Wires” – Althlete:
    http://www.youtube.com/watch?v=MPUlichsfQg
    (nyoprinces, you especially are gonna need tissues)

    “He’s My Son” – Mark Schulz: (apologies in advance)
    http://www.youtube.com/watch?v=azt2MdViON8

    And in the “Country May Be Cheating” Category:
    “Oklahoma” – Billy Gilman:
    http://www.youtube.com/watch?v=m0aW1CQslDk

    “He Didn’t Have to Be” – Brad Paisley:
    http://www.youtube.com/watch?v=BjO1F6oCab8

    • http://twitter.com/TwoBusy TwoBusy

      Wires is a great, great, great song – and an excellent call.

  • Janice
    • http://twitter.com/highlyirritable Jeni M

      My 13yo cracks at James Blunt almost every time!

  • Cindy

    Natalie Merchant’s Beloved Wife. Gets me every time. Also, Judy Garland’s version of Have Yourself a Merry Little Christmas. There’s something about that line “if the fates allow”.

    • http://twitter.com/highlyirritable Jeni M

      Judy Garland = :(

  • http://twitter.com/jenunexpected Jen T.

    “Travelin’ Soldier” by the Dixie Chicks. GAH. http://www.youtube.com/watch?v=nLBgmbXBOb8

    And “A Place Called Home” by Kim Richey. Which I can’t even listen to anymore because I listened to it incessently during my divorce and now it just kills me. http://www.youtube.com/watch?v=4axvOqxRu54

    • http://twitter.com/highlyirritable Jeni M

      I love Travelin’ Soldier. Her voice is so pure, it sends chills.

    • FadraN

      ME TOO on that one.

    • http://twitter.com/chisherman Chi Sherman

      Had completely forgotten about Kim Richey! We’re getting reacquainted on Spotify and YouTube now. :)

  • http://twitter.com/resident_hippie Resident_Hippie

    How about I will Follow You Into The Dark by Death Cab For Cutie? My Beloved Wife is another, already mentioned.

    • http://twitter.com/highlyirritable Jeni M

      Excellent sad-off contenders, both.

    • MollyGMartin

      That Death Cab song SLAYS me.

  • http://www.facebook.com/traceygaughranperez Tracey Gaughran-Perez

    And oh my god, THIS: http://www.youtube.com/watch?v=xQx-6cUyHVo *dies*

    • http://twitter.com/TwoBusy TwoBusy

      So very, very happy you just pulled out The Blue Nile. Well played.

      • http://www.facebook.com/traceygaughranperez Tracey Gaughran-Perez

        It makes me beyond happy that you are here to appreciate. :)

    • Tania

      Let’s Go Out Tonight is the soundtrack to every dramatic scene of my life. ‘Cause everyone scores their own life, right?

      • http://twitter.com/xotrace Tracey

        Only the best people. ;)

  • Miss Banshee

    My (now completely dementia-addled) grandma singing “You Are My Sunshine” *drops mic*

    • http://twitter.com/highlyirritable Jeni M

      …slow clap… Well played, Miss Banshee.
      WELL PLAYED.

    • http://baltimoregal.blogspot.com/ baltimoregal

      Win. although, Johnny Cash’s version is pretty good.

  • KellyBDelaney

    “Martha” by Tom Waits

  • Miss Banshee

    Oh, there’s also this, in case you still have tissues. http://www.youtube.com/watch?v=MmM7B-M3LVg

  • Christina Alva

    This gets me every flipping time, had to take it off the iPod: India.Arie – Ready for Love

    http://youtu.be/mxkMlS2nuU8

    Oh, and this turns me weepy immediately: American Tale – Somewhere Out There

    http://youtu.be/l_iRdgGZ6Xc

    For full tear effect, you have to play film version, not the James Ingram/Linda Ronstadt version

    • http://profiles.google.com/kemi.like.chemistry Kemi Sutton

      Oh, yes. “Somewhere Out There”. ALWAYS.

  • FadraN

    If this doesn’t make you cry, you are dead inside or something. (And it has to be this video version too)

    “I’ll Follow You Into The Dark” by Death Cab for Cutie
    http://youtu.be/jEGXU773tTM

    • http://twitter.com/highlyirritable Jeni M

      This one’s getting a lot of votes…

    • http://baltimoregal.blogspot.com/ baltimoregal

      The ENTIRE “Plans” Album.

  • FadraN

    And I have to add this one by Tori Amos, “I Can’t See New York” http://www.youtube.com/watch?v=tmUJOnf_Ce0

    Now I’m off to listen to the others and cry my eyes out.

  • jay

    Agreed about Just Breathe by Pearl Jam…the first time I heard it, I just put my head on the desk and waited til the deluge stopped. I’d like to bring Elvis Costello’s God Give Me Strength and Bob Dylan’s Tangled Up in Blue (harmonica points) to the table as well.

  • Miss Banshee

    Pullin’ out the big guns now. Get ready. http://www.youtube.com/watch?v=IZbN_nmxAGk

  • http://twitter.com/ryenerman ryenerman

    Years ago I insisted my husband play literally anything OTHER than the John Prine CD we were listening to on a long drive. I couldn’t take the sad for even one more moment after about 7 songs. The urge to just jump out of a moving car was nearly overwhelming. He’s that good.

    • http://twitter.com/highlyirritable Jeni M

      Isn’t he the best/worst?

  • kelly

    “Coat of Many Colors” as sung by Dolly Parton will make me weep.

  • http://www.facebook.com/alimartell Ali Martell

    Okay. So. We have been obsessed with Les Mis the last few weeks, and like a total loser, I weep my fool head off every time they get to the damn epilogue. I swear to god, big awful tears.

  • Amy Jo

    Pretty much anything by Harry Chapin, but Taxi gets me every time!

    http://youtu.be/c5dwksSbD34

    • Missy

      Oh, Taxi! I could cry THINKING about that song!

  • Lia Adams

    Late to the party, but Jeff Buckley’s Hallelujah and Elliot Smith’s Miss Misery will kill me every single time!

    • DianaCLT

      Hallelujah is amazing. I’ve heard so many versions by so many people. It’s one of those that just grabs your heart and soul and doesn’t let go. ?

    • Snarky_Amber

      Jeff Buckley’s Hallelujah is a cover of a Leonard Cohen song. DISQUALIFIED.

  • Ed

    “This Woman’s Work” by Kate Bush.

    • DianaCLT

      I loooove this song. So amazing how few know it.

  • Irma

    Thank you for including a 35 year old Gordon Lightfoot song on your list. It was beautiful then, and it still haunts me now. (And don’t even get me started on Bonnie Raitt…)

    Just bought my tickets today for a Leonard Cohen concert. Jealous???

    • http://twitter.com/highlyirritable Jeni M

      Do they sell uppers at the snack bar?

  • DianaCLT

    Good grief. I Can’t Make You Love Me. Fall, 1991. That was the soundtrack to my freshman year of college nervous breakdown (childhood skeletons in closet fell out…plus boyfriend I’d fallen head-over-heels for was cheating), the soundtrack to my big bro marrying his high school sweetheart…only to be divorcing 6 months later (my mom still refuses to listen to it), the soundtrack to my dad’s business investment going to shit and parents almost losing their house. Fuuuuck. Amazing song. I don’t get sad anymore, when hearing it. Now it makes me grateful that we all survived, and we’re all better for it.

    • http://baltimoregal.blogspot.com/ baltimoregal

      YEEEESSSS. Have you heard Adele’s version, though?

      • DianaCLT

        Oh lawdy, no. Adele did this? I’m sure it’s heart-wrenching loveliness. Do I dare go there? Uhhhh…..

        *Slinks off to YouTube*

        • DianaCLT

          You hold no power over me, Adele (At least, not this time.)! It’s lovely, yes, but it feels rushed to me. In Bonnie Raitt’s version, it feels like she’s still in the middle of being broken. Adele’s is nice, but it just sounds like singing to me.

          • http://baltimoregal.blogspot.com/ baltimoregal

            Oh, yeah. It’s no Bonnie. But it is good.

  • Claire

    Adam’s Song by Blink 182 and My Reply by The Ataris get me every single time. can’t get links as on my phone but check out my reply, it’s his response to a letter an eating disordered girl sent him while she was in hospital and giving up on life. so sad!

    • http://twitter.com/highlyirritable Jeni M

      Oooh, good call on the Blink 182. I like that it’s so matter-of-fact and not mushy.

  • http://twitter.com/jennamariebee Mrs. Jenna

    How has no one said “Black” by Pearl Jam?!

    https://www.youtube.com/watch?v=JfhsRIDh1RQ

    • http://twitter.com/highlyirritable Jeni M

      Pearl Jam needs their own category. Like one of those “Trivial Pursuit” special editions.

  • http://twitter.com/MamaKaren Karen

    I suspect the country music cry-off would be contest in and of itself.
    I submit- “The Walk,” Sawyer Brown http://www.youtube.com/watch?v=p4c9Iyu4feg

    “Concrete Angel” or “Broken Wing,” Martina McBride http://www.youtube.com/watch?v=dgjTO5eAbZY http://www.youtube.com/watch?v=KtNYA4pAGjI
    The video for Concrete Angel ups the ante significantly.

  • http://www.facebook.com/rebekah.mills.52 Rebekah Mills

    I’m a little late to this discussion, but if you need a few more sad songs, I have plenty to recommend. One of my favs is “The Final Cut” by Pink Floyd – it’s not the original band line up that most prefer, but the loneliness and despair described by the voice of a soldier returning to his regular life after being at war breaks my heart. Along with that I would have to include “The Piano” by PJ Harvey, which tells the story of a girl witnessing her mother being murdered by her father in front of her with a hammer – extremely disturbing and sad, but beautiful at the same time. Lastly, I throw out “Play Crack the Sky” by Brand New, although several of the songs from their album “Deja Entendu” would fit the sad requirement, this song closes the album giving an analogy of a relationship’s death as a ship doomed to sink and the desire to drown rather than survive. Haunting and achingly sad lyrics finish the song with “I know that this is what you want./A funeral keeps both of us apart./You know that you are not alone./Need you like water in my lungs./This is the end.” Love the idea of this as a game – can’t wait to listen to all the other suggestions made above. :)

    • http://twitter.com/highlyirritable Jeni M

      Murder+Hammer= Can’t lose this game!

  • mrsladybird

    I’m an amateur compared to all of these, but “First Family” by Rich Mullins always brings tears, particularly around the 1:45 mark.

    [youtube http://www.youtube.com/watch?v=xA6bBEDzFdo&w=560&h=315

  • http://www.facebook.com/profile.php?id=525936928 Ed Horch

    Coming in a close second to TWW which I posted earlier, “Levon” by Elton John.

  • MollyGMartin

    This post, this game — WIN. Ben Folds’ “Carrying Cathy” destroys me.

    • Snarky_Amber

      Missing the War/Evaporated. I bawl. EVERY. TIME.

  • tadpoledrain

    James Keelaghan, Captain Torres.
    http://www.youtube.com/watch?v=4kcPjpzxsMw
    It’s worth it just to listen to him tell the story. That’s enough to set me off. And then the thing about the answering machine, and I am done. I just made the mistake of watching the video, and now I’m a mess.

  • http://southernfriednewjersey.com/ Trixieplum

    “The House That Built Me” – Miranda Lambert (the line about the dog buried in the yard gets me every time).

  • crabby appleseed

    I cannot believe I am nearly two weeks late to this thread, there are 78 comments, and not one single person mentioned The Promise by Tracy Chapman.

    • http://twitter.com/highlyirritable Jeni M

      This was a good one! Some many I forgot, like “Anything by Bob Dylan.”

  • http://baltimoregal.blogspot.com/ baltimoregal

    WHAT IS “Yellow Ledbetter” about? And why is it so LONG? “Garden” by Pearl Jam gets me though.

    ***”Bad Reputation” by Freedy Johnston. If you don’t know this go listen right now.

    “Let it Be” by the Beatles is my #1 crying song though if you insist on discounting Leonard Cohen because nothing is better for crying (for me) than Johnny Cash singing “Bird On a Wire.”

    • http://twitter.com/highlyirritable Jeni M

      “Let it Be” *is* good for a box of tissue or two…