Can Jack in the Box’s New Pineapple Express Milkshake Top The Mighty Oreo? We Investigate

Last year we reviewed and ranked 14 different milkshakes from 14 different fast food chains in search of the thickest and tastiest. Our ranking revealed to us that Oreos are probably the single best thing to ever happen to the milkshake, and one of the finest Oreo Milkshakes comes from the stoner paradise that is Jack in the Box (ranked fifth!).

But what about those other Jack in the Box milkshakes? In addition to the mighty Oreo Shake, Jack also makes vanilla, chocolate, strawberry, and beginning yesterday for a limited time, the 4/20 themed Pineapple Express shake. The Pineapple Express Shake is a spin on the vanilla shake blended with pineapple syrup and topped with whipped cream and a maraschino cherry. Sort of like a Dole Whip.

Upon the shake’s announcement, Seth Rogen — writer of Pineapple Express — took to Twitter to make it clear that he had nothing to do with the milkshake and Jack in the Box did not contact him about using the name.

We’re not sure Jack in the Box needs to get permission for something like this, but Seth’s point is valid. And he’s right about the tacos (though he forgot to mention that they’re delicious in the right context).

We’ll pick a side depending on how good this thing tastes, and since we’re grabbing the Pineapple Express we figured we might as well order every milkshake on the menu and rank them from worst to best. We’re also going to give a 1-5 score based on how good they taste dipped in fries, this won’t have any effect on where we rank the milkshakes, but we figured it’s good info to have if you like living life the fun way.

Can anything top the Oreo Milkshake? Are we team Seth or team JiB? So many questions to answer, let’s get sipping!

5. Vanilla

Calories: 580 (Reg. Size w/ whipped cream)

Tasting Notes:

Before we talk about what the JiB Vanilla Shake tastes like, let me just throw this out there — all of these shakes are good. JiB’s shakes are super thiccccc, so thick that it takes an annoying amount of effort to get them through the straw. They’re creamy, almost like pure soft serve ice cream, and they keep their consistency for a remarkable amount of time.

It takes a whole hour for this shake to start to break down, that’s pretty amazing. Having said all that, JiB’s vanilla shake tastes… like nothing. There is the faintest hint of vanilla in there, but clearly, this shake is more of a foundation for the other flavors, which I’m pretty positive are just this shake, plus a flavored syrup.

It works for all the other flavors, but it makes the Vanilla stand out as tasting like it’s missing something.

Fry Dipability:

5/5. It might not taste like much on its own, but when encasing a salty french fry in its creamy goodness, few things taste better. This might be Jack in the Box’s best shake to dip your fries in. Ironically, we think it’s their worst tasting.

The Bottom Line:

Neutral to the point of flavorlessness. It’s sweet, refreshing, and creamy, with only a hint of vanilla.

4. Strawberry

Calories: 650 (Reg. Size w/ whipped cream)

Tasting Notes:

12-year-old me’s head would explode if they knew I would one day rank (the thought of ranking milkshakes as a job would also not compute to my 12-year-old brain) a strawberry shake above any flavor, let alone vanilla, every kid’s favorite. But I’m just going to throw this out there — disliking strawberry ice cream is kid shit.

It takes a mature palate to appreciate the complexity of artificial strawberry flavoring! That’s a hill I’m willing to die on.

This is a good shake, it’s remarkably refreshing and the strawberry flavor is faint enough that your tastebuds don’t really zero in on it, which helps to mask the fact that artificial strawberry doesn’t really taste anything like real strawberries. It’s an improvement in every way to the Vanilla because it actually tastes like something.

When paired with the whipped cream and maraschino cherry, this shake has an ice cream sundae quality to it. If Jack in the Box wanted to shake things up (pun intended) they’d find a way to work banana into this shake and give us one of the greatest milkshakes in all of fast food.

Seriously, why haven’t they done that yet?

Fry Dipability:

2/5. It just doesn’t really work. Nobody likes a salty strawberry. [Though that does sound like a cool band name. -ed]

The Bottom Line:

It tastes like the ‘80s vision of the ‘50s. It’s comforting, warmly nostalgic, and classic, and you should drink it while listening to some good ‘ol rock and roll.

3. Pineapple Express

Calories: Not listed, but it’s safe to assume it hovers in the upper 600s.

Tasting Notes:

I went into this milkshake fully expecting it to be gross. I’m not sure if it’s because I have an affinity for Seth Rogen’s Houseplant weed brand and wanted to be on Seth’s side here, but it’s hard to hate this thing. It could’ve tasted terrible, a sickly sweet and tangy overload of candied flavor to match with Jack in the Box’s menu of weird stoner delights. But like all of the milkshakes, it’s subtle, and that’s its strength.

The pineapple syrup adds a gentle tartness and a fruity body to an otherwise neutral-tasting milkshake. It doesn’t really pair well with the whipped cream because it has a sort of Big Stick Popsicle flavor to it. If Jack in the Box added a cherry syrup in there, this shit would truly be next level.

The Bottom Line:

Sorry Seth, but this is delicious.

Fry Dipability:

1/5. Even worse than the strawberry. The salty potato flavor doesn’t pair well with the subtle tang of this shake. It’s almost vomit-esque. Barf-adjacent.

2. Chocolate

Calories: 680 (Reg. Size w/ whipped cream)

Tasting Notes:

It tastes just like a scoop of chocolate ice cream. I’m not sure if it was just my particular milkshake, but this was the only shake out of the lineup where I could visibly see the flavored syrup, and that added visual definitely enhanced the experience in some small way.

I’m almost positive this is just chocolate syrup mixed in with the Vanilla Shake base, but I can taste two distinct flavors of chocolate here, a more chalky milk chocolate powdered flavor, and a syrupy chocolate sauce flavor. I wish JiB would take the extra step to drizzle some chocolate sauce on the whipped cream, or maybe add a side of crushed nuts to really bring this to the next level and add some texture in there, but we’ll take what we can get.

Fry Dipability:

4/5. It’s good, just not as good as dipping a fry in vanilla.

The Bottom Line:

Almost a perfect milkshake. If not for our number one pick, this would be the clear winner.

1. Oreo Cookie

Calories: 690 (Reg. Size w/ whipped cream)

Tasting Notes:

Going in I assumed this was going to hit number 1 (it’s why we include the shake in our best milkshake lineup) but tasting all the shakes side by side really put into focus how much better this shake is than all of the others. The Oreo Cookie shake has all of the best qualities of every other shake in this ranking, it’s thick, sweet, creamy, refreshing, but it has one thing the other milkshakes lack — texture.

This makes a world of difference. When the Oreos come up through the straw and melt on your tongue in a bath of sweet and creamy vanilla ice cream it’s decadent dessert ecstasy.

Fast food milkshakes rarely get better than this flavor combination (though a few chains do the Oreo shake even better) and because Oreos are kind of a dusty cookie, the granules of chocolate cookie pepper the entire ice cream base, so aside from the actual chunks of Oreo you drink up from the straw, the milkshake itself tastes like cookies and cream ice cream. It’s a significant improvement to the neutral vanilla base it’s built upon.

Fry Dipability:

3/5. Unfortunately dipping a french fry in an Oreo shake makes neither the shake nor french fry taste any better. It’s fine, but should only be tasted out of curiosity.

The Bottom Line:

JiB made the Oreo Milkshake a standard flavor in the lineup of fast food milkshakes everywhere, and we count the OG amongst the best of them. Every other Jack in the Box milkshake lives in the shadow of this one. It’s the only one worth ordering.

Find your nearest Jack in the Box here.