SoulBounce’s Top 50 Michael Jackson Songs: #37 ‘You Can’t Win’

You get in way over your head
And you only got yourself to blame


Before he sang "Leave Me Alone" or "They Don't Care About Us," Michael Jackson told us how "You Can't Win" when it comes to a system of injustice. This politically-steeped song was, ironically, one of the central musical numbers in the '70s motion picture The Wiz where MJ made his acting debut as he matured from being the pre-pubescent lead of the Jackson 5 to a highly successful solo artist.

Despite what you may read on Wikipedia or other movie sites about the success or lack thereof of the movie, I can tell you that the movie theaters in DC were packed as folks sat shoulder-to-shoulder to watch this highly-anticipated movie featuring the glamorous Diana Ross and the very popular Jackson. It was 1978 and I was barely four-years-old, forced to sit on my mother's lap to watch the movie because the theater was sold out and there was no seat available for me. Unfazed, I didn't care. I was going to see Michael Jackson, who, at that time, like now, was my number one favorite singer of all time. On the screen, costumed as the ingenious Scarecrow, Michael grabbed my starry-eyed attention as he opened his mouth to croon the song "You Can't Win," which is, hands-down my favorite song from the movie's soundtrack. Only he could have a full theater of people groove to an upbeat song about being frustrated and kicked around. That must have been the reason why the song was written specifically for MJ to sing, replacing the song originally sung by the Scarecrow character in the stage play that the movie was based on. Released as a single in January 1979, "You Can't Win" was released as the second single from The Wiz: Original Motion Picture Soundtrack, a double album distributed by Motown Records in September 1978 that I still own to this day on vinyl.

As I listen and sing along to this tune, nothing is more haunting as we think of Michael's death and listen to the trailing chorus that sings, "You can't break even, you can't get out of the game." However, we know, that like the Scarecrow, triumph is inevitable and like his straw-filled character, Michael showed us how it was not only possible to win, but create a legacy that lives on for a lifetime.

Michael Jackson: "You Can't Win"

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6 Responses

  1. Embarrassed to say I was also 4 years old when my mother took me to see The Wiz but we didn't get far in the movie to see the Scarecrow because I was afraid of the Munchkins and cried so loud we had to leave the theater.
    Do love this song.

  2. i loved the wiz and i loved this song. michael's "whoo!", the crows, the whole thing.

  3. I love this song and movie. I wasn't born until the 80's and didn't experience the wiz until I was elementary age, but it has ranked as one of my favorite movies ever since. I loved MJs version of the scarecrow and this song will forever be part of that memory. This era in general is my favorite for his voice maturation. I really appreciate you doing this countdown and thoughtfully examining the song, it's been a highlight in my day for a while now. Looking forward to where my favorites rank.

  4. LMAO @ 2damnfunny
    my daughter was afraid of this movie too for the longest time. She is now a Michael Jackson like her mama and can watch eyes open.I admit, those subway thingys scared the begeesus out of me and gave me nightmares.

  5. Nice, Soulbounce............Its funny how l literally watched this video of him singing this song, and said to myself the night before ya'll posted this, "You Can't Win better be on this list......and if it isn't THEY ARE BUGGIN'." And then you post
    Anyway, of course I frickin' love this song. It's the good ole' blues and he sang the hell out of it. I get chills when he hits that deeper note at the end cause its so funky and soulful. I keep replaying that part over &
    Besides that, I have a little info about this song that a lot of people don't know. I think it was during the Thriller era, when he released Billie Jean as a single, they put this song on the B-Side. Only it's just the second half of the song. I guess Quincy had him go in the booth to just change the "you can't get outta the game" to "you can't get outta the rain." So then that's what they called the "new" song, "Can't Get Outta The Rain." So its basically the same song just with a few new vocal overdubs. I love discovering stuff like this. And just for anybody who's a real fan like me to the point of almost obession, that would want it just to have it is:
    Lastly, my only beef with this post is that this song shoulda been higher. But then again, I'll have to see what the rest of the list looks like.

  6. Best song off of the soundtrack! Definitely from what I would call his 'Golden' Era!


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