How To Run A Cakewalk That Takes The Cake

If you're not sure what a cakewalk is, you're not alone: I once sat on neighborhood board that wanted to include the activity at a holiday party, but I had to consult Wikipedia to figure out what the hell a cakewalk actually entailed. Little did I know that several years later, I myself would be running the cakewalk at my kids' school.

Basically, a cakewalk is musical chairs with cakes. Numbers are placed on the floor and music is played. Music stops. Number is picked. If you are standing on the same spot as that number, then you get to pick out a cake from a packed bench of generous cake donations. And you get a cake! And you get a cake! The cakewalk actually has a considerably long history, according to NPR: It stems from a pre-Civil War ritual performed by African-Americans on plantation grounds who were making fun of the plantation owners' fancy promenades. It's where the phrase "takes the cake" comes from, also, obviously, "it's a cakewalk," indicating a prize won by doing something easy, like stepping on a numbered square.

I can take no credit for establishing this fun school event though; it was already begun by a fun family in our neighborhood, the like-minded, music-savvy souls who are my family's co-hosts for our annual karaoke party. They are the ones who truly put the cakewalk on the map, now eight years running. So when they had to be out of town for the craft fair this year, our names were tossed out as replacements. Frankly, I think it's just because they knew we had the necessary audio equipment.

Still, I am not a great baker, and neither my husband Brian nor myself are known for our incredible patience with children (just ask our kids). Our incredibly generous and well-organized friend came over with all the gear—laminated floor numbers, set-up map, cash box—to conduct cakewalk training. Comments like, "it should be pretty easy; after all, it's a cakewalk!" were thrown around a few times to mild hilarity.

Now that I am a cakewalk veteran on both sides of the laminated numbers, I find that this fun community activity offers some valuable life lessons. Also, there are definitely right ways and wrong ways to run a cakewalk.

The first year I brought a cake to the cakewalk, it was a straight-up delicious apple cake I had been really into that season. Unfortunately, it sat there on the cake bench, as painfully unloved as a wallflower at prom. I had failed to realize that small children don't care about homemade apple goodness: They care about gaudy, colorful frosting, with as much visible chocolate as possible. Eventually my apple cake was selected by the kind president of the local school council, who assured me later that it was in fact delicious. But I never made that mistake again. The next year I went straight to the supermarket and bought the flashiest cake I could find: The one that looks like a mini-hot tub barrel, except the planks are Kit-Kats and the water is M&Ms.

Fortunately, as the cakewalk legacy has grown, a lot of our local families get more creative. Many kids spend that Friday night before the cakewalk happily baking their own creations, dolloped with inch-thick icing and holiday marshmallow Peeps and candy canes. Our first winner this year went straight for the cupcakes she had brought herself, all topped with candy cane sign posts that announced the North Pole. I couldn't really blame her.

The moral here is: Flash sells. If you don't want to be the last cake left on the table, you have to sparkle things up a bit.

Given my husband's musical proclivities, and the fact that we were going to be surrounded not just by children but their parents, teachers, and school administrators, I begged him to keep the playlist as squeaky-clean as possible. We had learned that painful lesson years ago at a block party, accidentally playing the non-radio-friendly version for DNCE's "Cake By The Ocean" as horrified parents looked up aghast. The kids were going to march around the cakewalk regardless, but songs like Beyonce's "Single Ladies" and Bruno Mars singing "Uptown Funk," beloved by parents and kids alike, made things a lot more enjoyable. A crowd soon formed, stretching the cakewalk line all the way back to the gym. Apparently "I Believe In A Thing Called Love" by The Darkness held up better than I was expecting.

I had a heart-stopping moment when a Skrillex song came on. "Isn't there a swear in this song?" I asked Brian. "It's at the end," he assured me. We love the Beastie Boys as much as anybody, but you just have to watch out for the profanity at a school event. But for the final round, Brian went ahead and played Jesus Lizard's "Then Comes Dudley," a dirge that seemed to reflect how wiped out everyone was by that point.

Is this a cakewalk or a cake dance, you may be asking? Actually, kind of both. Thanks to everyone's generosity and ingenuity, we had about five dozen cakes to give away. There were so many, in fact, that we started giving away spirit awards to the best cakewalk dancers in special double-cake rounds, for fear of leftover cake (which I refused to take home). A friend of my son's has feet that barely seemed to touch the ground, immediately walking (dancing) off with the first spirit prize.

The spirit award also allows you to mess with the games of chance a bit. We folded and refolded the numbers, we had totally impartial people pick every time, and yet, for a while, space number 11 was on quite the winning streak. I don't think, in dozens of rounds, we ever picked number two. The same kid won three times. The rules of fate are fickle.

At our cakewalk training, our friend noted how every year, he and his wife disagreed about maybe just calling out the number of the little kid who's on their fifth try and really wants that cake. He protested, claiming to wanting to keep the integrity of the cakewalk intact. I could definitely see his wife's point, but Brian steadfastly agreed with our friend. "Oh, absolutely," he declared. "There will be none of that bullshit," he said, waving away the tears of a kindergartner who just wanted a brightly decorated cupcake with sprinkles.

The spirit award is a way around this. Really, if someone is willing to dance their heart out for a cake, I am inclined to give it to them. To get that crying kid her cake, you can also make up titles like a congeniality award. But then, fate is a cruel mistress and maybe the cakewalk is a good place for kids to learn this stark yet valuable lesson. You can absorb a lot about life at a cakewalk.

In the end, I think we ran about 40 cakewalk rounds, with 15 people paying $1 per round, and made about $600. Yes, it's not going to balance the district budget or anything, but it added some festive fun to the craft fair. After handing over the money to the school council treasurer and packing up the laminated numbers, I went home for the biggest nap of my life. Unfortunately, my son had already headed to our house with his friends and their winning cakes, so that I was instead plagued by sugar-crazed boys playing laser tag. Still, the young girl who had made that particular chocolate cake was delighted when I showed her the picture of how the boys had demolished it... all for a good cause, of course.