7 Of The Cringiest Holiday Hip-Hop Songs

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holiday hip hop songs
NEW ORLEANS, LA - JUNE 29: Rapper Master P at 2017 Essence Festival - Celebrity Charity Basketball Game at Xavier University Convocation Center on June 29, 2017 in New Orleans, Louisiana. (Photo by Paras Griffin/Getty Images)

Some of these lyrics should have stayed in the drafts.

Christmas is nearly upon us, and the air is already charged with its magic. It’s the season of festive cheer, twinkling lights, and timeless tunes that typically propagate the holiday spirit. However, nestled among the jolly classics is a subgenre that elicits reactions ranging from amusement to secondhand embarrassment. This, folks, is the realm of cringey holiday Hip Hop songs.

Hip-hop artists traverse a fine line between catchy celebration and unbearable awkwardness when they try to weave their lyrical magic into the fabric of Christmas traditions. While some find the sweet spot and create magic, others, unfortunately, end up with offerings Santa would frown at. Thankfully, the list of great holiday Hip Hop tracks is longer than that of the cringy ones. For example, Ye’s “Christmas in Harlem,” and Jeezy’s “Hustlaz Holiday” are getting a spin this season. However, there are still quite several uncomfortable songs in existence, and the following seven take the cake.

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7. “Christmas Song” – Juelz Santana Ft. Skull Gang

“Christmas Song” was released as a part of Jim Jones & Skull Gang's compilation album A Tribute To Bad Santa Starring Mike Epps in 2008. The Christmas-themed Hip Hop album contains 19 songs. However, “Christmas Song” particularly stands out. While it features a catchy beat, the lyrics of the song are unbelievably corny. Can one really listen to “Wrap your lips and tongue around me / I’ll slide my gift under your tree” with a straight face? Getting through the song is quite a task because listeners will wince for most of it. It is admittedly quite groovy, but even that is not enough to save it from being terribly cringy.

6. “Christmas In The Ghetto” – Master P & C-Murder

The concept of this song is certainly an interesting one. However, it’s hard to say its execution was handled properly. Listeners can already tell a few seconds into the song that it may not offer much. Unfortunately, it disappoints even more than expected. From the horrendous chorus to the verses about robbery, drugs, and ghetto tales, there’s a disconnect. Despite the artists’ efforts, it is one of many meager holiday Hip Hop songs, and a chore to sit through. “Christmas In The Ghetto” appears on the 11-track mixtape, Westcoast Bad Boyz: High Fo Xmas released in 1994.

5. “How Sean Price Stole Christmas” – Sean Price

Beginning with a sample of the classic “You’re a Mean One Mr. Grinch,” this song tells a story that’s a little too detailed. To his credit, Sean Price completely embodies the character of Mr. Grinch, expressing his abject hatred for Christmas. However, his narration and descriptions go maybe a bit too far, making the song a not-so-pleasant listening experience. Nevertheless, some may find it intriguing, or even enjoyable, but they are likely in the minority. Despite its Hip Hop bounce and impressive delivery, this is not a holiday song you’d want to play in most gatherings.

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4. “Jingle Bellz” – Juelz Santana & Starr

With “Jingle Bellz,” Juelz Santana and Starr had an opportunity to create an unforgettable holiday song. The song was meant to be a smooth blend of Hip Hop and R&B elements. However, it ended up being just another badly written cover of a classic Christmas tune. While Starr delivers impressive vocals, its impact is countered and overshadowed by lackluster lyrics. Additionally, Juelz Santana delivered a forgettable verse, and his presence is barely felt on the track. The pair squandered the chance to make a great song, and turned it into a cringy materialistic tune instead.

3. “The Christmas Song” – David Banner Ft. Marcus & Sky

David Banner’s holiday Hip Hop offering contains an interpolation of the Christmas staple “Tidings Of Comfort And Joy.” Besides its catchy beat, that’s arguably the only comforting or joyful thing about this song. “It’s winter time and we steal, cannot find a job / We fill out applications, but you treat us like we’re slobs / So we rob and we steal, we’re just trying to get a meal…” so goes the song’s chorus. Without a doubt, it’s a catchy song. However, justifying theft, even in a song, is not a good look. “The Christmas Song” would be one of the best holiday Hip Hop songs around if only it had been written differently.

2. “Deck My Balls” – Afroman

Afroman’s cover of “Deck The Halls” is an acapella track, and contains arguably the most outrageous opening line on this list. If “lick my b*lls with lots of saliva” doesn’t make you cringe, I don’t know what will. Although Afroman goes on to say some less outrageous things, it’s impossible to recover from his opening line. The song barely exceeds a minute and a half, but it certainly deserves its spot on this list. The absence of a beat makes it impossible to ignore Afroman’s words, so there is no saving grace.

1. “Christmas Grind” – Killer Mike

We’ll come out and say it. If listeners only take the beat and Killer Mike’s delivery into consideration, this song is a hit. However, things begin to get dark pretty quickly when attention is paid to the lyrics. Not only does Killer Mike say he will rob people, but he also outlines how exactly he’ll go about doing it. Certainly, that’s not the kind of Christmas grind anyone should be focused on. Besides the interpolation of the melody for “Carol Of The Bells,” nothing about this song spells Christmas or cheer. “Christmas Grind” is one of the most inappropriate holiday Hip Hop songs out there.

About The Author
Demilade Phillips has been a Features Writer for HotNewHipHop since 2023. The self-proclaimed music fanatic deals with most things Hip Hop and R&B, while also covering film, television, and the entertainment industry at large. When he’s not working, the International Relations graduate is either binging anime, immersing himself in the underground EDM scene, or crafting up original pieces.