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Judged by the Cover - Ugly Christmas Sweater

There is no shortage of Christmas albums…covering everything from traditional hymns to some of pop cultures finest trying to create music that evokes the feelings of the season. Most of these album covers have your traditional Christmas elements (Christmas trees, presents, snowflakes, red and green colors, etc…)…but there is also no shortage of “interesting” finds. So we are going to explore a few of them that I find to be most unusual in this special edition of the Judged by the cover podcast.

A very special Christmas album cover, album cover

A Very Special Christmas

To kick off our ugly Christmas sweater episode, I have an album cover that I have always found to be odd, but I didn’t realize how important this album was until I got into the. The album, A Very Special Christmas, is a compilation album that came out in Oct of 1987 and it has some huge names on it… for example….Madonna, sting, Whitney Houston, U2, RUN DMC….and much much more!! These are some of the biggest names of the MTV era of music, and their contributions to this album shaped how pop culture and Christmas music sound and go together. It also made it “cool” in the eyes of artist… SO much so that now if you name any big artist today…Taylor Swift, Ariana Grande, Bob Dylan, John Legend…they all have Christmas albums. You can also think of it this way…without this the now Christmas Mega Hit “All I Want For Christmas” may have never existed…..which now that I think about it, might not be a bad thing….but I digress….back to the album.

The album producer, Jimmy Iovine, created this album as a tribute to his beloved father who loved Christmas and the holiday’s, who tragically passed away in 1985. Bruce Springsteen had called Iovine to offer his condolences, and kind of reacting in the moment said to him “I’m going to make a christmas album…Jimmy also wanted to keep this album pure, and keep money out of the equation, so he had to find something to due with the proceeds of the album. Of all things Jimmy found his organization to give the proceeds to at a Special Olympics wrestling event. It was a charity event, and they didn’t have or couldn’t get the “real” wrestlers so they had actors playing their roles. He believed in what the Special Olympics was trying to do, so they decided all the proceeds would go to that origanization.

This album spawned 10 more albums, and collectively (as of dec 20, 2022) has raised $145 million dollars for the Special Olympics!!!

Now let’s talk about this album cover. I will start by stating that it’s not terrible….I guess my main gripe with it, is that it doesn’t scream (or even whisper) Christmas to me. Iovine enlisted the help of pop artist and world celebrated graffitist Keith Haring to design the cover art.

Keith Haring, art, style, modern art
Example of Keith Haring's art style

Keith Haring was an American artist that emerged from the New York City graffiti subculture of the 1980’s. HIs style was simple and animated imagery that usually was outlined figures (people, dogs, shapes, etc…) and was also usually very colorful with thick black outlines. He also used lines to show movement or animation similar to those you would find in a comic book.

The cover has a bright red background with gold art and lettering. The main art piece is described as a haloed figure cradling a child. If you can image a simple outline drawing of a person, holding a baby…thats surrounded by a box that in a nutshell is what we have.  Around the main figures head we have lines that would indicate light, or possibly excitement.

I’m guessing that the meaning of this is a play on the original Christmas story of Mary holding Jesus…but given this is also a very “cultural” album, with proceeds going to the Special Olympics…it could also be celebrating the specialness of a child or of all children. Although in and of itself it is a great art piece…I struggle to see “Christmas” in this. I know that I for one struggle to understand some modern art styles, but I just don’t get the Christmas vibes. I love the hard work, the intentionality, and the mission of the album…but unfortunately I don’t love the cover art.

The same artwork would continue on for all the albums, in one form or another, and in different colors and styles. I will share some of them on the Notes page for this episode. You can find the blog post with all the digital content for these episodes at and look for the post corresponding with this episode.

So that’s our first Ugly Christmas sweater album, what do you think of this album cover…?

Happy Holi-dee

he next victim…I mean album cover fits into the category of awkward family photo worthy. Do you remember when the “awkward family photo” style took over the internet, and actually became its own greeting card style…? If you are unsure of what I’m talking about a quick scroll through the website will answer all your questions.

The album in question here is titled Happy Holi-dee, by Lenny Dee. You catch that fun pun there…..

Lenny Dee was an American virtuoso organist who played many styles of music. His albums were mostly categorized as easy listening and space age pop. Surprisingly there isn’t a lot of info on the internet regarding this album, but thanks to the YouTube channel LP & Laundry, I got this information about the album. From the back of the album it describes it as such…”Organist Lenny Dee, about the merriest music maker you’re apt to meet south of Santa’s workshop, presents in this album a sparkling collection of the most popular Christmas songs.

As for the cover…boy is there a lot of fun stuff to discuss. We have ole Lenny Dee himself dressed up as Saint Nick….minus the beard (which we will discuss that more in a sec). and not like some people who just throw on the Santa hat and red clothing, he is in the full Santa suit with the big black belt, the long white hair and of course the hat. He is posing with not 1 or 2 but 3 toy poodles, all of which have this I don’t want to be here stare. And you have some Christmas presents in the shot and for a last nice touch there is a snow flake and a star in the top right corner.

SO back to the no beard….I can imagine a couple of reasons for the no beard, but it kind of feels like a cop out to me. If you’re going to commit to the full Santa up-fit…you gotta do the beard too. Now a couple reasons why I image he didn’t do the beard, first being the dogs. I can’t confirm this bit of info but I’m guessing these are his dogs (because he was supposedly a big fan of poodles)…and they probably wouldn’t want to participate in photos with him in a beard. Also and probably a more important reason is people being able to recognize Lenny Dee since his image is/was his brand.

Speaking of these poodles, they are staring away from the camera, off to the side where I’m sure someone is trying to get their attention so it looks like they are staring at the camera. It adds to the awkwardness of this photo and gives the dogs this stone cold look of “please get us out of here”.

If you are ever digging through some old vinyl and find one of these albums, it’s actually a pretty fun listen. Again shout out to the YouTube page LP & Laundry for his play through of the album. It always helps to get to listen to an album when you’re looking to discuss or dissect it.

Ella Wishes you a Swinging Christmas

Boy did I save the best for last. Although there is a lot of interesting imagery out there on Christmas albums. I feel there is none out there quite as “unique” as this. The one beautiful thing about Christmas music as a theme, is that there is a lot of imagery that you can use that will make people think of Christmas, or invoke Christmas memories of the past….but would you consider using a unicorn as the main image on your Christmas album….? Neither would I…but Ella Fitzgerald did.

In 1960 the album Ella Wishes You a Swinging Christmas was released by Ella Fitzgerald. Ella Fitzgerald was an American jazz singer, and has been referred to as the Queen of Jazz, the First Lady of Song, or Lady Ella. Ella is noted for here purity of tone, impeccable diction, phrasing, intonation, and for having a “horn-like” impovisational ability to her singing.

One review I found of the album said this…”Rich, mellow sound, ear-pleasing arrangements, and of course Ella Fitzgeralds good cheer make this a Christmas season winner your sure to play often at least until the 25th of December and perhaps beyond. I can definitely agree, after doing a listen through its a pleasant album to listen to…and kinda makes me want to get a copy of this on vinyl…because Christmas music just sounds better on vinyl.

But the cover…..O the cover….where do I begin. I will again give the same disclaimer that I gave on the first album, it’s not terrible as an art piece. It’s a lil wierd, but definitely not terrible. But as a Christmas album cover….I don’t it just have those Christmas feels.

The main part of the cover is this painting of a unicorn with its head popping up out of what looks like long HUGE blades of grass, with a flower in its mouth. The unicorn is in this modern painting style that is….interesting. the way they textured the body in the painting almost makes it look like its got a lot of eyes all over its body….The color on the unicorn is these yellow and orange shades with the lines outlining the imagery being purplish in color.

The font usage is also kind of interesting because at the top it has “Ella wishes you” in pretty traditional handwritten font, but the rest of the album title is wrapped around the head of our unicorn in a very hand drawn font in a light purple color. My one kind of complaint with the hand drawn font is that the G’s kind of look like 9’s….especially the one a the end of swinging. Also how they had to stack Christmas because they ran out of room isn’t ideal either in my opinion.

I did find one forum of people discussing this album, and it seems that initially the album was supposed to have a track called “Rudolph the Psychedelic Unicorn” or possibly a song called “Unicorn Song”. I can’t validate the claims…but may be the best explanation of why there’s a unicorn on the front of this album.

I also saw some people talking on another forum about Ella’s manager and label co-owner Norman Granz, and had this to say about him “Verve’s label owner Norman Granz is likely to have been responsible for the choice of this album’s artwork. His admiration for modern and abstract art is evident in the artwork of other Verve albums, and possibly on this album, too. Along with the man’s own tastes, a PR strategy could have been behind the selection of the album's so-called wild modern design.” It sounds like he was trying to use modern art in album covers to make them kool, because the pr messaging at the time was basically “that albums such as this one were cool, exciting, “in tune with the times,” not old-fashioned.

I'm assuming that the album cover may not have been Ella's first choice, and she possibly had no choice, but I would love to hear your thoughts of this album cover...? Let me know below.

Have a Merry Christmas, and a Happy New Year!!

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