A coworker asked me to make an anniversary cake for her first anniversary.

I (stupidly) suggested that we try to make a smaller, scaled-down version of her wedding cake... forgetting that she had cupcakes at her wedding. This got her going and she decided that she wanted a two tier cake (8 & 6) with cupcakes on the sides- but not just any cupcakes, she wants cupcakes that look like the ones she had at her wedding. They had a plethora of cupcakes... German chocolate, mint chocolate, cookies and cream, cheesecake, red velvet, carrot cake, etc. She specified that she wanted the sides of the cupcakes on the side of the cake and the tops to show when you look down at it.

I'm not intimidated by cupcakes, but I'm certainly intimidated by the idea of doing this cake. I'm not sure how to handle it! She requested a carrot cake with cream cheese frosting. Would I paint the cupcake silhouette on? Use fondant? A combination? And the tops... dear Jesus, I'm baffled.

Please help me figure out how to tackle this cake!

i would make chocolate liners by pouring melted choco into cupcake liners--letting it set up and trimming them to a nice size (in half or more) to adhere to the sides of the cake--all the way around

then i'd mimic the type of icings

or i'd cut 'cupcake wrappers' out of pleaty fondant--i'd make it look pleaty with an impression mat

I like your chocolate liner idea. Do you mean that they should be 3D, almost like they're popping out of the side of the cake?

yes--that's what i was thinking --kind of leaning out of the side of the cake--popping out

because otherwise the idea of making that many flavors is making me weak ;)

and you could just re-melt the cut off pieces

and you can test with plain cupcake wrappers to determine the best angle

andmaybe use a hot knife to cut the chocolate ones they way you want them