Gregory is a masterful musician and any of their songs are perfectly catchy.
- "Way Deeper Down"
, a catchy song starring the three skeletons of Undertale. It's all so perfectly in line with each character: Sans' playful yet not-so-subtly threatening Hurricane of Puns, Papyrus' more lighthearted, boastful and endearingly clumsy bars and Gaster's dark sadistic verse still holding onto the mystery surrounding him. - "Find the Keys" and "Art of Darkness", chronicling Bendy and the Ink Machine, are appropriately dark, yet incredibly fun and fast-paced. The songs describe the tragic and gruesome legacy of Joey Drew Studios, perfectly encapsulating the nature of the games while still being extremely catchy. The latter video shows off Gregory's voice-acting chops as they provide unique voices to Joey (though he doesn't sing as him), Henry, the Lost Ones, the Butcher Gang and Bertrum Piedmont.
- "The Fine Print" and "A Matter of Factories". Rapped from the perspectives of a Corrupt Corporate Executive, it waxes lyrical about the the company's greed and cruelty.
- "Rip and Tear (My Way to Your Heart)". Vastly different from Doom and even Stupendium's usual fast-paced rap fare, it is still a humorous and strangely heartwarming love song.
- The House Always Wins, an insightful look into the dark mind of Mr House as he wistfully introduces himself and decries American society, with a lovely soft rhythm.
- "Vault Number 76". More hectic than its Fallout predecessor, it features a Stupendium barbershop trio as the main character slowly loses their mind.
- Virtually any of their collaborations with other artists. The MINECRAFT VS LEGO Rap Battle rivals ERB for the best rap battles on the entire web (they even got Lloyd and Peter to help out). The beat and lyrics match up well and will make you want to dig out the old Minecraft and Lego pieces.
- "Nook, Line, and Sinker" is a fantastic Villain Song presenting Tom Nook as a snobbish yet cunning Morally Bankrupt Banker who has all the islands and villagers under his thumb. The song is somewhere between a rap and a waltz, with a beat made from the sound of coins falling (as pointed out by a YouTube commenter). One of the coolest parts is near the end, where the beat stops and is replaced by light, elegant strings. The whole song manages to be both refined, with a bit of restraint, and yet totally sinister at the same time, helped by the Stupendium's excellent voice acting.
- "These Hallowed Wings", in contrast to Tom's scheming, is a fun, light-hearted vibey tune presenting Blathers as he guides the player through the museum and describes his humorous mishaps.
- "Rogue's Gallery" returns to the dark ominous theme as Crazy Redd, speaking in an Italian accent, speedily raps like a combination of a mafiaso, a snake-oil salesman and a battle rapper, detailing his criminal schemes and knowledge of paintings and artists.
- "The Most Fashionable Faction", a collaboration with Harry101UK, gives all nine playable characters in Team Fortress 2 a chance to rap about their individual prowess. Yes, that includes the Pyro. Though the Stupendium admitted that their vocal range doesn't go low enough to mimic the Soldier and the Heavy, Harry steps in to rap for those two, as well as to provide the incredible visuals in the music video showcasing the plethora of incredible ensembles the characters can wear.
- "The Apex" is a stunning track featuring NemRaps covering Hitman 3. It not only features some cleverly placed puns and reveals some more ways Agent 47 can eliminate you, but also devotes a section to Nem, who packs in amazing wordplay, lyric flow and rhythm as a Providence operative trying to beef up his security against 47, only for that assassin to successfully kill him anyway. All of that is backed up by a chilling beat appropriate for the game it is based on.
- The entirety of A Little Heart based on Kingdom Hearts III captures all the elements that make the Kingdom Hearts franchise so good while boasting at least 60 Disney song titles in its lyrics. All the best trying to find them all...
- "The Data Stream" is their tribute to Cyberpunk 2077, specifically the Corpo starting origin, detailing the pervasiveness that Arasaka has accomplished in the society of Night City, bragging about how much influence they have over their customers simply because no one is in a position to stop them. All the while, Cami-Cat provides vocal accompaniment in places and sings the chorus, and the whole track has a tight synth-infused dubstep beat that provides a Retraux take on modern music.
- "Fragments" is an uplifting song covering Ratchet & Clank: Rift Apart and including multiple references to the franchise as a whole, but it also delivers the complex yet fundamental message that change, while it can be scary, is ultimately for the better, and sometimes, it takes a different perspective to see the good things in a new and unfamiliar situation.
- "Shine Through", a truly joyful song based on Life Is Strange: True Colors that encourages you to make the best of the world, even when things might seem sober and blue, finding love in those you surround yourself with, and using colors as a motif. The music video is also gorgeous, using various light tricks to brighten up the Welsh mountainside.Whenever your Life is Strange and
The pain is too much to go through
Know that you can find your Haven
In those you've chose to be close to
'Cause we'll find the brightest colours
When we look inside each other
This life is more vibrant for the
Ones who find the light to shine through - "And to All A Good Fright" is festive and warm while also being creepy, fitting for the Stupendium intending to do something else for Christmas only for the horror Characters to demand them to make a song for them to enjoy the festivities.
- "Ad Infinitum" is a song, in the technical term, from the perspective of Spamton G. Spamton. "Fever Dream" doesn't even begin to describe the lunacy. Forgoing referencing Spamton's music except for a brief 'Big Shot' reference when he first laughs, the backing track is a thumping techno track that goes perfectly with the obscenely fast rapping that perfectly sums up Spamton's twisted character. That, and the makeup and visual effects are insane and incredible.
- "The Toybox" has a deceivingly upbeat tune about Playtime Co.'s legacy. It's similar to their Bendy and the Ink Machine songs yet stands out on its own.
- "Milk Milk Lemonade", a tribute to Cuphead, takes Hurricane of Puns to a completely new level. It boasts about having over one hundred beverage puns hidden in its span of 3 minutes and 53 seconds, and stays true to its word.
- "A Pizza The Action", a self-proclaimed "Kickass 80s Action Anthem" for Five Nights at Freddy's: Security Breach. The song itself is a pun and reference-filled Spiritual Successor to David Hasselhoff's "True Survivor" with an homage at the end to Vincent Price's verses on "Thriller". However, the video has its own awesomeness, as The Stupendium duets with Cosmo the Parrot. Who is Cosmo the Parrot? A design for a FNAF character based on The Stupendium themself, made by one of their fans, and given life through the animation of Coda, one of the best animators in the FNAF fandom.
- "Open The Sky", a haunting tribute to Stray. The first verse is from the perspective of B-12, the second is the lament of the Companions, and the third brings both elements together as a powerfully emotional layered choir, interlaced with snippets of news reports and an increasingly desperate chorus.
- "The End Of The Line" is a delightfully spooky ditty about Choo-Choo Charles, with lyrics featuring oodles of train-based wordplay set to a subdued yet oh-so-very catchy backing track. Much like the game itself, "The End Of The Line" is a silly concept taken quite seriously, while still indulging in some dark humor.
- "Neath" is a dark yet catchy tune set in the world of Fallen London, following the laments of those now trapped beneath. The first two verses each follow someone longing for love, while the third verse focuses on Byron Brimstone, who is very much a human, and the fourth is from the perspective of Mr. Pages, one of the Masters of the Bazar. It also happens to be 12 minutes long.
- "The Ribbon" is a mind-bending rock opera about Alan Wake II and is sponsored by the creators of the game to help promote it. Liberally using the metanarrative perspective and fluctuating state of the fourth wall that the original and the sequel are known for, the song lays out the intrigue of Alan's current predicament, Saga's recent involvement, and what might wait for both of them as their journeys twist and turn amongst one another.
- "A Little Theorizing" is the post-November 2023 OFFICIAL theme song for Game Theory, and contains tons of references to popular episodes of the channel and sidechannels, classic and new alike. It comes across as a sort of nostalgic tribute to the channel, ending with a crowd chanting the phrase, "That's just a theory... A Game Theory!" And Matthew Patrick himself saying it at the very end.
