Dessert Tamales with Pineapple

Award-winning chef Bill Smith shares his exclusive recipe for a delicious holiday dessert.

November 30, 2011

You will need a steamer for this recipe.

  • 8 cups maseca (corn flour ground especially for tamales and tortillas)*
  • 4 teaspoons baking powder
  • 4 teaspoons salt
  • 1 teaspoon cayenne pepper
  • 2 teaspoons cinnamon
  • 1 ½ cups sugar
  • ½ cup brown sugar
  • One 14-ounce can of Eagle Brand condensed milk
  • 4 ½ cups whole milk
  • 2 cans (20 ounces each) of pineapple chunks
  • 1 2/3 cups unsalted butter, at room temperature
  • 1 package of dried corn husks, soaked in cool water for at least an hour

*You should be able to find all of the odd ingredients at Latino grocery stores.



1. Place the maseca, baking powder, salt, pepper, cinnamon, and sugars in the bowl of a mixer fitted with the paddle attachment. Mix for a few seconds to blend together.

2. In a saucepan, mix the condensed milk and the regular milk together. You will need 6 cups of liquid, so add more milk if you need to. Heat until good and warm (it needn’t be boiling hot).

3. In another saucepan, put the pineapple chucks with all of their liquid. Cook over medium heat until the liquid is nearly gone, but don’t let the pineapple brown. Set aside to cool down a little. Set the mixer on medium speed and feed the butter into the dry ingredients. It should be completely blended in. Feed in half of the warm milk in a slow steady stream. Then add the pineapple, little by little. Everything will try to get out of the mixing bowl. Just keep pushing it back in. Resist the urge to chop the pineapple up more. Feed in the rest of the milk and mix. The dough will hold together, but it will be stickier than regular tamale masa.

4. You have to eyeball each cornhusk. You are looking for leaves that are at least as big as your outspread hand. Lay a leaf on the counter with the longest dimension left to right, with the pointy end on the right. Put a 3-inch-long cigar of dough in the center of the leaf, leaving an inch or so of leaf at the pointed end. Fold the point over the dough, then roll the leaf around the dough. Fold the fat end back over the tamale and lay it flap side down in the steamer basket. Fill the basket as full as you can with tamales. It can’t be too crowded. When the basket is full, steam at full boil for an hour to an hour and 15 minutes. The tamales will be firm but still a tad squishy. Remove them from the steamer and let them rest for about 15 minutes. Bring them to the table in their husks.

Makes about 60 tamales

BILL SMITH has cooked memorable suppers for most everyone who lives, farms, or visits the good life in Chapel Hill, North Carolina. He is as well known for a New York Times Notable and Food & Wine Best-of-the-Best cookbook, Seasoned in the South, as for the way he tends to remember his customers' favorite dishes.

In both 2009 and 2010, the James Beard Awards named Bill Smith in the final four for Best Chef Southeast. And in 2010, The James Beard Foundation nominated Crook's Corner a Best Restaurant in the US. In 2011, the James Beard Foundation named the restaurant he's presided over for 17 years to be American Classic.