What Makes a Cake a Legend? Unpacking the Sweet Stories and Secret Ingredients of Three Unforgettable Desserts

Isn’t it ironic the way some cakes sort of stick with you? Not a recipe you made once or twice, but that cake. The one that appears at every family function, the one requested by name, the one that seems to get incorporated into the very fabric of memories. We all have them, or at least we’d like to. They’re not just sugar, flour, and butter; they contain stories, connections, and sometimes a little bit of surprise magic.

Mary Alisa Sherman’s Famous Chocolate Cake

Consider Mary Alisa Sherman. For forty years, she’s been baking a chocolate cake that is, quite simply, legendary in her community and her family. This is not merely a chocolate cake; it’s the chocolate cake, rooted in a secret recipe inherited from her godmother and honed by Mary Alisa over four decades of baking. It’s been the centerpiece of dozens of birthdays for her three kids and seven grandkids, adorned tables at historical society galas and community volunteer functions, and served as a sweet treat for her five older sisters – sisters, no less, who don’t even have the recipe! That sort of recipe, which was kept close for so many years, has a history baked into it.

But what began as a cherished family tradition took an unexpected, charming turn. Mary Alisa’s rich, tender confection, made with its deep, almost unsweet cocoa complemented by a whipped sweet cream cheese frosting, became the launching point for a late-in-life part-time profession and even acquired a new, memorable nickname: “Mary Alisa’s Dank Chocolate Cake.” It wasn’t intentional; it occurred organically, as a result of her son, Chris Sherman, CEO of Island Creek Oysters. He brought his mother’s cake to The Winsor House restaurant, which is owned by the Island Creek Oysters farm in Duxbury.

The cake first had to please executive chef Cosmo Goss, and originally, it was not going to be a regular item on the menu. As Chris Sherman wrote, he “frankly thought it was a special thing we could do for the opening.” They even had a fear of people not liking it, which is a natural concern when opening oneself up to public opinion. But the reaction was spectacularly positive. The online chatter and reviews began pouring in, each one saying the same thing: “You have to try the cake.” Four years on, it’s not only still on the menu; it’s a full-fledged hit.

These days, Mary Alisa prepares these three-layer wonders twice a week right there in The Winsor House kitchen. Over 1,300 cakes now since the restaurant’s opening in the fall of 2021, she remains over the moon with it. “I L-O-V-E it!” she says, with a sort of unadulterated enthusiasm that has you grinning merely reading it. She goes on, perhaps a little corny but all heartfelt, “I feel like I’m living in a Christmas Hallmark movie.” Her greatest delight? I adore seeing people happy with it.” The most rewarding moments are, she thinks, in the restaurant when others do not recognize her and she can see them eating or cutting the cake, their faces lighting up with smiles.

Keeping the quality that established the cake as a legend is of the utmost importance. Mary Alisa bakes each cake by hand, a process which testifies to the care and effort that goes into every single bake. She employs particular high-end ingredients: King Arthur flour, quality cocoa powder, sugar, baking powder, Kosher salt, oil, whole milk, expensive Nielsen-Massey vanilla, and white eggs. Why the white eggs? “It’s easier to find egg shells in batter with white eggs,” she reveals, a hard-earned tip gained over years of experience. And yes, there is a secret ingredient, one that she cannot share.

Mini Pineapple Cakes

This recipe creates delightful mini Bundt cakes featuring a caramelized pineapple base topped with a moist white cake batter made using a box mix and pineapple juice. The process involves cooking the pineapple, preparing the cake batter, baking, and carefully cooling the cakes before unmolding.

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Prep Time 10 minutes mins

Cook Time 45 minutes mins

Total Time 2 hours hrs 10 minutes mins

Course Snack

Cuisine American

Servings 6 people

Calories 4067.4 kcal

Equipment

• 1 Food Processor
• 1 Nonstick Skillet (10-inch)
• 1 Mini Bundt Pan Ensure it is well-buttered and floured.
• 1 Large Mixing Bowl
• 1 Electric Hand Mixer

Ingredients

  

Main

• One 3 1/2-pound pineapple peeled, cored and cut into 1-inch pieces* (see Cook's Note)
• 2 tablespoons pineapple juice plus 2/3 cup
• 1/2 cup packed light brown sugar
• 2 tablespoons unsalted butter at room temperature
• 3 egg whites
• 2/3 cup water
• 2/3 cup vegetable oil
• 1 1/2 teaspoons almond extract
• One 18.25-ounce box white cake mix recommended: Betty Crocker Super Moist

Instructions

 

• Place an oven rack in the lower 1/3 of the oven. Preheat the oven to 325 degrees F. Butter and flour a mini Bundt pan.
• For the Cakes: Place the pineapple in the bowl of a food processor. Pulse until coarsely chopped. In a 10-inch nonstick skillet, combine the chopped pineapple, 2 tablespoons pineapple juice, sugar, and butter over medium-high heat. Bring the mixture to a boil, stirring occasionally. Cook until the liquid evaporates and the mixture begins to brown, about 10 to 15 minutes. Spoon the pineapple mixture into the prepared pan.
• In a large mixing bowl, combine the egg whites, water, vegetable oil, almond extract, cake mix, and 2/3 cup pineapple juice. Using an electric hand mixer, beat the mixture on medium speed for 2 minutes. Pour the batter over the cooked pineapple. Bake for 28 to 30 minutes until the cakes begin to pull away from the sides of the pan and the tops are golden. Allow the cakes to cool for 15 minutes. Place a piece of parchment paper on top of the cakes. Put a baking sheet, upside-down, on top of the parchment paper. Flip both pans over and allow the cakes to cool completely while still in the Bundt pan, about 1 hour. Unmold the cakes and place on individual serving plates.

Notes

Ensure the mini Bundt pan is thoroughly buttered and floured to prevent the cakes from sticking. The pineapple mixture needs to cook until most liquid evaporates and it starts to brown; this caramelizes the fruit and intensifies its flavor. Do not rush the cooling process while the cakes are inverted in the pan; this allows them to set properly and prevents them from breaking when unmolded. Using room temperature butter for the pineapple mixture helps it combine more easily.

The frosting is the most important part, a sweet whipped cream cheese treat consisting of sifted powdered sugar, cream cheese, Land O’Lakes unsalted butter, and that same Nielsen-Massey vanilla. Mary Alisa purchases her ingredients herself, stocking up in local grocery stores when they are on sale and even ordering from Amazon. She transports her ingredients in Tupperware containers to the restaurant kitchen.

Baking is careful. The cake layers are baked for one hour and 15 minutes. Once cooled, she builds the layers and uses a crumb coat frosting. A quick 15-minute freeze is next; she states that this short freeze keeps the cake from moving as she add the last, liberal layer of frosting. The finishing touch is shavings of Cadbury Royal Dark chocolate on top. She bakes at least four cakes every week, and sometimes up to eight, depending on demand.

Mary Alisa has become something of a local celebrity in Duxbury, affectionately known as the “Cake Lady.” Her fame extends beyond the town lines, too. She has a rather famous customer: Steve Carrell. She’s made a “few whole cakes” for him, particularly around Christmas, though she notes, “I’ve never met him.”

Her daughters are more delighted than anyone else about this new phase in their mother’s life. As Elise Sherman so eloquently expressed it, “I love how my mom can now share this piece of our childhood with her community.” Her twin, Devon Daley, noted, “It was a sacrifice for my mom to stay home with us. It was meaningful.” Watching her do something she loves now is just as meaningful. “Second lives can happen organically.”

Mary Alisa’s pre-cake fame included life as a child in Connecticut, relocating to Duxbury in the ’80s, working at a software firm, and obtaining a graduate degree in education and a Spanish teaching certification. She is still an active volunteer, a Duxbury history guide, and was formerly a South Shore representative for The Fresh Air Fund. She and her husband, Chris senior, regularly hosted a child. Now, it’s her son, Chris junior, who’s her boss, and he makes sure their work relationship is grounded in warmth, always including a message like “Hey Mom, Hope you’re having fun!” in the memo line of her paychecks.

The Power of Rediscovered Recipes: Big Mama’s Cinnamon Roll Poke Cake

Taliking of popular, semi-mysterious cakes with interesting histories, the r/OldRecipes Subreddit is a goldmine of food history and community bonding. Standout recipe that was shared in 2022 by user HumaWormDoc is for a cinnamon roll poke cake, lovingly dubbed Big Mama’s Secret Cinnamon Roll Cake after their grandma. This cake promised everything good about a cinnamon roll without the normal mess, and based on feedback from the community, it did not disappoint.

What is a poke cake, anyway? Once the cake is baked, holes are poked into the top with a skewer. While the cake is still warm, a liquid is poured over the top. The liquid seeps into the holes and gives flavor throughout. It’s a genius trick for ensuring a bite of cake in every bite.

Big Mama’s version, however, channeled the cozy, comforting flavor of cinnamon rolls. The appeal is simple: it tastes just like the gooey, sweet insides of a cinnamon roll, arguably the best part! Looking at the recipe ingredients, you can see why it delivers on sweetness: the cake batter calls for 1-1/2 cups of sugar, and the icing adds another 2 cups of confectioners’ sugar plus milk, butter, and vanilla. That’s a lot of sweetness packed into one dessert, making it undeniably rich and perfect for sharing with a crowd because a little slice goes a long way.

Overnight Cinnamon Rolls

This recipe details how to make rich, fluffy overnight cinnamon rolls. It features an enriched dough, a cinnamon-brown sugar filling, and an overnight cold fermentation step for enhanced flavor and convenience. The rolls are baked until golden and finished with a classic cream cheese icing, perfect for breakfast or brunch.

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Prep Time 45 minutes mins

Cook Time 30 minutes mins

Total Time 11 hours hrs 45 minutes mins

Course Breakfast

Cuisine American

Servings 12 people

Calories 7627.1 kcal

Equipment

• 1 Stand mixer with whisk and dough hook attachments
• 1 Large Bowl
• 1 Rolling Pin
• 1 Serrated Knife
• 1 9x13 inch Glass Baking Dish

Ingredients

  

Main

• 4 large egg yolks room temperature
• 1 large whole egg room temperature
• 2 ounces sugar approximately 1/4 cup
• 3 ounces unsalted butter melted, approximately 6 tablespoons
• 6 ounces buttermilk room temperature
• 20 ounces all-purpose flour approximately 4 cups, plus additional for dusting
• 1 package instant dry yeast approximately 2 1/4 teaspoons
• 1 1/4 teaspoons kosher salt
• Vegetable oil or cooking spray
• 8 ounces light brown sugar approximately 1 cup packed
• 1 tablespoon ground cinnamon
• Pinch salt
• 3/4- ounce unsalted butter melted, approximately 1 1/2 tablespoons
• 2 1/2 ounces cream cheese softened, approximately 1/4 cup
• 3 tablespoons milk
• 5 1/2 ounces powdered sugar approximately 1 1/2 cups

Instructions

 

• For the dough: in the bowl of a stand mixer with the whisk attachment, whisk the egg yolks, whole egg, sugar, butter, and buttermilk. Add approximately 2 cups of the flour along with the yeast and salt; whisk until moistened and combined. Remove the whisk attachment and replace with a dough hook. Add all but 3/4 cup of the remaining flour and knead on low speed for 5 minutes. Check the consistency of the dough, add more flour if necessary; the dough should feel soft and moist but not sticky. Knead on low speed 5 minutes more or until the dough clears the sides of the bowl. Turn the dough out onto a lightly floured work surface; knead by hand about 30 seconds. Lightly oil a large bowl. Transfer the dough to the bowl, lightly oil the top of the dough, cover and let double in volume, 2 to 2 1/2 hours.
• Combine the brown sugar, cinnamon and salt in a medium bowl. Mix until well incorporated. Set aside until ready to use.
• Butter a 9 by 13-inch glass baking dish. Turn the dough out onto a lightly floured work surface. Gently shape the dough into a rectangle with the long side nearest you. Roll into an 18 by 12-inch rectangle. Brush the dough with the 3/4-ounce of melted butter, leaving 1/2-inch border along the top edge. Sprinkle the filling mixture over the dough, leaving a 3/4-inch border along the top edge; gently press the filling into the dough. Beginning with the long edge nearest you, roll the dough into a tight cylinder. Firmly pinch the seam to seal and roll the cylinder seam side down. Very gently squeeze the cylinder to create even thickness. Using a serrated knife, slice the cylinder into 1 1/2-inch rolls; yielding 12 rolls. Arrange rolls cut side down in the baking dish; cover tightly with plastic wrap and store in the refrigerator overnight or up to 16 hours.
• Remove the rolls from the refrigerator and place in an oven that is turned off. Fill a shallow pan 2/3-full of boiling water and set on the rack below the rolls. Close the oven door and let the rolls rise until they look slightly puffy; approximately 30 minutes. Remove the rolls and the shallow pan of water from the oven.
• Preheat the oven to 350 degrees F.
• When the oven is ready, place the rolls on the middle rack and bake until golden brown, or until the internal temperature reaches 190 degrees F on an instant-read thermometer, approximately 30 minutes.
• While the rolls are cooling slightly, make the icing by whisking the cream cheese in the bowl of a stand mixer until creamy. Add the milk and whisk until combined. Sift in the powdered sugar, and whisk until smooth. Spread over the rolls and serve immediately.

Notes

Ensure all cold ingredients like eggs and buttermilk are at room temperature before mixing; this helps yeast activate properly and improves dough texture. Knead the dough until it's soft and moist but not sticky – this is key to tender rolls. The overnight cold proof develops flavor and makes the dough easier to handle. Using a shallow pan of boiling water during the second rise creates a steamy environment, resulting in incredibly soft, puffy rolls. Bake until the internal temperature is 190°F to avoid dry rolls. Sift powdered sugar and use softened cream cheese for the smoothest icing.

Big Mama’s rendition replicates the sticky, sweet center of a cinnamon roll. The batter is 1-1/2 cups of sugar, and the icing adds another 2 cups of confectioners’ sugar along with milk, butter, and vanilla. Nutty and irresistibly sweet, a small slice serves a long way.

The instructions are simple and lenient. It involves self-rising flour, eggs, vegetable shortening or unsalted butter, sugar, milk or buttermilk, and vanilla extract. Half of the batter is spread in the pan, then a cinnamon brown sugar filling, then the rest of the batter, and a swift whirl. The frosting involves heating milk and butter, and stirring in sugar and vanilla, and is then poured over the warm, pierced cake.

The versatility of the recipe is part of its appeal. Redditors have cut the sugar, substituted flours, and tried mix-ins such as banana slices or chocolate drizzle. Big Mama herself played around with the recipe.

The Legend of the Tunnel of Fudge Cake

These tales of rediscovered classics aren’t exclusive to internet forums. One such example is the Pillsbury Tunnel of Fudge cake, which was introduced in 1966 and contributed to making the Bundt pan famous. Developed by Ella Helfrich, the cake had a runny, underbaked center and was a cultural phenomenon.

But the recipe disappeared when Pillsbury stopped producing the essential ingredient: Double Dutch Fudge Buttercream Frosting Mix. Home bakers attempted to reverse-engineer it for decades without success. That is, until Pillsbury food scientist Mallory Edwards reverse engineered the original frosting mix with only five ingredients: powdered sugar, cocoa powder, cornstarch, vegetable shortening, and salt.

With a chocolate exterior and a creamy, fudgy interior, the Tunnel of Fudge was back to life. Mallory’s sculptor, cake decorator, and pastry chef background, coupled with her love for food history, helped decipher the secret.

These cake tales Mary Alisa’s beloved family recipe, Big Mama’s comforting poke cake, and the resurrected Tunnel of Fudge illuminate the lasting bond between food, memory, and community. They demonstrate that great culinary experiences are all about starting with a simple idea and a whole lot of heart.