Wintley Phipps

The Second Day of Mellowmas: O Holy Wintley!

Jeff: Well, well, well! Look who’s back for more Mellowmas.

Jason: I can’t say no to you, baby.

Jeff: As it turns out, ending a sentence with “baby” is oddly appropriate for today’s song. Also unnecessary exclamation points.

Jason: I hope you’re not implying I use exclamation points unnecessarily. I would argue that every exclamation point I use during this holiday is justified.

Jeff: Oh no. I’m just saying that the album we’re covering today is titled “O Holy Night!”
Which, you know, seems unnecessary.

Jason: I agree with you. At the same time, find me something about the music we listen to this season that isn’t unnecessary.

Jeff: Jason, have you ever heard of Wintley Phipps?

Jason: Of course! My favorite song was “You’re In Love.”

Jeff: *looks at Jason quizzically*

Jason: You’re in love! That’s the way! It should be! ‘Cause I want you to be happy!

Jeff: *cackle*

Jason: Oh, wait. I see. Not them. Somebody else.

Jeff: Now I’m picturing a bald black man wearing Carnie Wilson’s beach lingerie from the “You Won’t See Me Cry” video.

Jason: There’s a very obvious joke here that I’m going to leave alone.

Jeff: I will join you in this. We are maturing, because Mellowmas makes us so old. Oh, speaking of old, here is a man with a very deep voice.

Jason: He’s definitely not from my family. Because we have very high voices.

Also, this guy is black.

Wintley Phipps

Jeff: I don’t know anything about Wintley Phipps, but I think he might be a minister.

Jason: He has a nice smile.

Jeff: He does! It’s almost as nice as Jeffrey Osborne‘s.

Jason: The star to the right of his album photo should actually be placed on his teeth. Just a killer smile.

Jeff: YES! He uses Topol.

Jason: I don’t know, Jeff. If I had a smile like that, I might use an exclamation point too.

Jeff: You might. And yet you would still sound nothing like Wintley Phipps. Hey, do you have a subwoofer?

Jason: I want to lie and say no.

Jeff: Turn it up and brace yourself for a night most holy. Are you ready?

Jason: I think the question is less if I’m ready and more if the people who live below me are ready.

Wintley Phipps — O Holy Night! (download)

Jason: A majestic opening. Classy.

Jeff: Live strings! Such a blessing during Mellowmas.

Jason: Yes! I like it so far!

Jeff: *cackle*

Jason: Wow.

Jeff: I can’t.

Jason: That’s pretty low.

Jeff: Seriously, if I was in the audience for this, I would be pissing my pants. They would kick me out.

Jason: Jeff, this guy has chops!

Jeff: He’s awesome! I know!

Jason: Here comes the good part. FALL ON YOUR KNEES!

Jeff: But there’s something about this voice that makes me laugh uncontrollably.

Jason: This is the part where I always think of Cartman.

Jeff: Yes! “O night…when I get presents…” Wintley Phipps is SMOOTH.

Jason: So I’ll give you that his voice is low. But he’s nailing this.


Jeff: He’s nailing it, but I can’t stop laughing.

Jason: I was NOT expecting that! Wait a second. Real strings, and a drum machine?

Jeff: A real drummer can’t compete with Wintley!

Jason: If you made it far enough to pay for the orchestra, why wouldn’t you just spring for the drummer?

Jeff: There’s no bass, either! The orchestra was down the street. Wintley overpowers all.



Jason: I just woke up the people downstairs.

Jeff: I’m sure they don’t mind, either. Wintley has risen. Goddamn! How many seconds are that last note?


Jeff: I bow before Wintley Phipps! All hail the Mellowmas king!

  • Jay Nagy
  • mlk

    His voice is low, but there’s nothing wrong with it. The drum is a little out of place, but not too distracting. Overall, I don’t think it’s much different from the Jim Nabors version, which you guys slayed a few years back.

  • Beau

    Sounds kind of like Taran Killam spoofing Scotty McCreery in the classic Michael Buble Duets SNL sketch a couple of years ago.

  • dslifton

    This was quite nice, and far too early in the season for a Mellowmas Miracle.

  • rockymtranger

    Seriously, this guy sounds like Thurl Ravenscroft who sang “You’re a Mean One, Mr Grinch.” Wow.

  • MatthewBolin

    Speaking of Cartman, I think he actually sounds a lot like Isaac Hayes. I expected him to end the song by saying “Hello, children!”

  • jasonhare

    I agree. Wilson Philips really came through.

  • MatthewBolin

    Don’t let Billy Baldwin know you misspelled his wife’s last name (2 “L”s), or he’ll come after you like….like a Baldwin.

  • trow125

    Interesting fact from Wikipedia: Phipps “was guest soloist at Diana Ross’ wedding ceremony in Switzerland.”

  • Rob Wynne

    We need a word for a post like this. I’m going to propose


    The feeling of intense disappointment once has when something you expected to be entertainingly awful turns out to instead be of high quality.

  • jefito

    I had completely forgotten that was the Nabors song we covered. Perhaps I was drawn to Wintley’s version subliminally.

  • jefito

    I thought the same thing!

  • jefito

    Only Mellowmas can make a person sad about hearing something that’s kind of nice. We’ve poisoned all of you.

  • arensb

    What could be more Mellowmas than poisoning the entire month of December?

  • jefito

    That’s a very good question.

  • DwDunphy

    Sliding into January, for one…DON’T YOU DARE.

  • Dennis Corrigan

    I’m worried that you guys are off your game this year. I mean, this Mellowmas is off to a not terrible start. Yesterday was bad but only in that way that generic tween pop is bad. And this was tolerable to not bad. And now I’m going to go hide because I fear the hellacious Mellowmas wrath that I might have just provoked.

  • jefito

    You probably should.

  • nedmassey

    First thing I thought of, too.

  • trow125

    The great Joe Queenan, in his book “Red Lobster, White Trash and the Blue Lagoon,” already coined such a fake German word. From an excerpt I found online (and it sort of has a Mellowmas connection!): Technically speaking, there is no English phrase or idiom to describe the feeling to which I refer, so here I will take the liberty of coining the term scheissenbedauern. This word, which literally means “shit regret,” describes the disappointment one feels when exposed to something that is not nearly as bad as one had hoped it would be. A perfect example is Neil Diamond’s recent album, “Tennessee Moon.”

  • Rob Wynne

    *grin* I am familiar with the book and Queenan’s term. This goes further, though, because it isn’t only not as bad as one might hope, but genuinely good. :)

  • Guest

  • Jay Nagy

    Oh, that messed up. But it should probably read: