With a Summer vacation upcoming, an annoyed Mario is forced to wait while Toadsworth "upgrades" the cannon outside of the castle. While waiting, Mario questions why there is a cannon in the courtyard, a flashback shows Mario attempting to use the cannon, only to hit the wall of the castle. Toadsworth finishes the upgrade (aka adjusting the power level) as Princess Peach comes outside ready to leave. Toadsworth tricks Mario into jumping into the cannon by throwing a plate of spaghetti in it. He tells Mario that the vacation doesn't need any "annoying Italians." Peach asks if Toadsworth didn't put too much power. As Mario is blasted off into space, he says he put a "loadsa power" in the cannon. The Mario Head makes a cameo appearance for a few seconds, staring at Mario while the latter is flying in space.
Meanwhile, Bowser is with SMG3 in their "Secret Evil Lair", from which he's controlling a satellite in space via a monitor, and tries to find the "secret of the universe." SMG3 calls him a "dumbass" while Bowser is searching, to which he replies by saying, "Hey, shut up." Bowser then notices Mario on the monitor, his head being so huge Bowser doesn't even recognize him. Static is shown while a black silhouette appears with a female chuckle, which soon goes back to normal except Mario isn't there. Bowser then goes to search for "the force" and tells SMG3 to feed the Chain Chomp(s).
Mario wakes up on the Comet Observatory, saying, "Chicken? Is that you?" A Luma then appears in front of his face, startling him and causing him to jump off the Observatory and commit suicide. Then he later reappears, meeting Rosalina. He is glad that he can stay in the Observatory with Rosalina and spaghetti, but when she asks "What's a spaghetti?", Mario freaks out and then jumps out of the Observatory again to commit suicide.
Later, Bowser is flying with his Clown Car, trying to find the "weird force", complying that he can use to take over the world. Then, Kirby is also flying on his Warp Star in space. The two don't notice each other, as they crash into their selves.
Back at the Observatory, Mario commit suicide multiple times, but every time he does, he regenerates later. Then he complains why won't the world let him die, only for Rosalina to reply that she was going to take him back to Earth. But Mario refuses, and still tries to die. Rosalina was about to get the Observatory to move, but Bowser and Kirby fly in, causing Bowser's Clown Car to crash into the Beacon.
As soon as the crash occurs, Rosalina looks in distress, while Mario finally wakes up from killing himself many times. It is clear that the clown car crashed into the power source of the observatory. Kirby refocuses himself and gets up after the crash. Next to him, Bowser is seen crying for what he did, with a old man luma saying "Nice job, d*ckface!"
Two police Lumas then come in and try to arrest the King of the Koopas. A hoard of Lumas come in to help, but they all bounce off Bowser's shell, making Bowser itchy. Rosalina then comes and tells the Lumas to calm down. She then questions Bowser and asks if he is an enemy. Bowser defends himself by saying that the pink gumball (Kirby) made him crash into the observatory. Of course, Kirby punches him because it is a lie.
Mario then comes into play and tells Rosalina that the enemy is Bowser and that he sucks at being evil. Bowser adds on by saying that he stole a princess, but only for two minutes. Rosalina seems to accept this fact, but says that the trip back to the planet would be delayed for 2000 years because the clown car crashed into the observatory. Mario panics after hearing about it and tries to commit suicide only to by blocked by a janitor Luma.
Bowser and Kirby fight when the a pair of speakers at the library begin playing. The lumas knew it was storytime and entered the library. In the library, Rosalina finished reading a book but Mario]] wants to go back. The lumas still want storytime so Mario forced Bowser to read for them. Rosalina and Mario leave the library to get the Wormhole Generator, a device created by E. Gadd to jump across the universe. Rosalina gives Mario the task of charging the generator exactly 90 seconds, which he accepts. She then leaves to check the Lumas.
Back in the main room, Bowser is seen reading bedtime stories to the lumas, where Rosalina sits to watch the action. In the meantime, Mario sees the old man luma holding a Super Mushroom and chases after him, leaving the Wormhole Generator unattended. Rosalina then wakes up from her bed, and notices that Mario overcharged the generator. Rosalina then asked Mario if he shot the gun already, to which he proceeds to do. Rosalina then tries to stop Mario, but it was then too late.
As a result of the shot, Mario created a blackhole, which starts to suck in the observatory. As soon as Bowser sees the blackhole, he freaks out. Rosalina then comments that there would be no way to escape from the disaster. All of a sudden, Mario notices something in the sky, which is Captain Steve, who would try to save the crew from the observatory, only to fail because the blackhole sucked him in.
Meanwhile, Bowser is seen showing his feelings to Kirby, who is left with a shocked expression. Just then, Bowser's satelite station appears, and proceeds to call SMG3. The koopa king asks SMG3 to hit the buttons on the satelite, in hope that it will find a way to save the observatory, but SMG3 refuses to do so because he believes Bowser is trying to make him look like an idiot. Bowser then pranks SMG3 by saying that he used his toothbrush as a toilet cleaner, to which he rages and presses the many buttons on the monitor, causing the satelite to block the blackhole. This is seen by Rosalina as a chance to escape.
Mario goes to assist Rosalina and leaves the Wormhole Generator to Kirby's assistance. However, Kirby sees it as a lolipop, and obviously eats the device. The result is a huge laser that sends the Observatory away from the blackhole and back into earth.
Meanwhile, Toadsworth and Peach are seen relaxing on their vacartion, with the latter commenting on how unusual it is without Mario. The observatory then crashes onto the island, much to the shock of the royals.
When the observatory crashed beside the island where Toadsworth and Peach is, Mario appears and demands to know who sent him to space, with Peach pointing to Toadsworth. In another room, Mario is seen shoving Toadsworth's head into the fire place, Peach and Rosalina getting to know each other, and Bowser reading more stories to Kirby and the lumas.
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- The title of this video might be a reference to a Super Mario 64 mission by a similar name: "Shoot to the Island in the Sky", where, like in the game, Mario needs to shoot himself to an island, Mario is shot into the observatory in the sky via a cannon.
- Mario floating in space with an alien robot may be a reference to one of Mario's deaths featured the blooper "101 Ways for Mario to Die (The Right Way!) 50,000 subs!", a scene which itself comes from the short video "Super Mario 64 Short: Long Jump" (without the robot however).
- SMG3's "Secret Evil Lair" from the blooper "Bad Star's Back! 300k Special" reappears in this video, but it's the first time its interior is seen, and it's revealed Bowser lives there too.
- When Rosalina interrupts the monitor at Bowser's and SMG3's lair, Mangle's garbled static from the video game Five Nights at Freddy's 2 can be heard.
- When Rosalina appears for the first time, a video error causes her to be partially invisible for a few seconds. As SMG4 was tired because he finished the blooper on Monday evening, he noticed it too late the next day, and then made a note for all to ignore this glitch.
- This isn't the first time the "partially invisible" glitch happened, though. It happened for a single frame with Dr. Mario earlier in "R64: A Dose of Dr. Mario".
- Despite playing a minor role in the video "The Wacky Wario Bros.: The Winning Ticket..", this is Kirby's first major role in a blooper of SMG4.
- While Kirby is flying on the warp Star, the English version of the Kirby: Right Back at Ya! theme song can be heard until he crashes into Bowser.
- It's revealed in this video that Mario acquires a new body (identical to his previous one(s)) when he revives after committing suicide. This might be how the other characters of SMG4's bloopers survive fatal deaths.
- When the numerous Luma are angrily staring at Mario after he said their "Mama" (Rosalina) has other things to do than relating them stories, a blue Luma is seen asleep and not reacting except it blushes along with all the other ones around it.
- This is the second time Kirby imagines an object as food, the wormhole generator in this case. The first time he imagined Waluigi's Rubber Ducky as fried chicken in the video "The Winning Ticket.."
- This is the second time Steve appears as Captain Steve, the first being in the blooper "SM64: ṩṩἔᾗмὄḋᾗᾄʀ 7 (TOAST edition)." However, it's the first time he's seen failing while using this alter-ego.
- It's also unknown what his ultimate fate was after being in the black hole, but it's unlikely he survived.
- The place where Toadsworth and Peach are spending their summer vacation is apparently located somewhere around America, most likely near the United States, as it's towards this country that the Observatory is seen flying when it approaches Earth near the end of the blooper.
- This is the first time in 2015 that SMG4 changes to the font text used now, but changes back to original 2014 font text, not until SM64: War of the Fat Italians 2015 (600k Special).
- This is the last blooper to show Bowser and SMG3 working together.