Supplies: shorter stubby terracotta pots (I found some at Home Depot & some really cool short stubby ones at Fred Meyer), spray paint, acrylic paint, clear spray sealer, rocks (for drainage), potting soil, plants, drill (with 1/4" drill bit), 1/4" dowel (Hardware store or Walmart), saw blade, round wooden balls (hardware store). Also needed, but not pictured: wood glue, paint brush.
OK, the painting part: I used spray paint. I like a quick job. BUT, the terracotta pots are very porous & you're not going to get an even coat with the spray paint. I sprayed my pot 2 times & I like the uneven faded look of it. If you want a more even, solid covering of color, use at least 3 coats of acrylic paint or latex paint. (Got any extra exterior housepaint in the garage? Perfect!)
When the "cherries" are dry, drill a hole in the bottom. Or you could do the drilling BEFORE the painting. I guess I did it backwards. Mine came with a tiny hole pre-drilled in the bottom, but it wasn't nearly big enough. 
Fill the hole with wood glue & insert the dowel. Poke it in the ground to dry. 
Now you can work on the details of your pot, which you'll paint with brown acrylic stripes to resemble a cupcake liner.
When the stripes are dry, seal the pot--inside & out--with the clear spray paint sealer. This is probably the most important step. Without a good seal, the water could cause your paint to bubble or eventually chip & flake off. Lots of coats of paint & a good sealer are the key to keeping your terracotta pots lovely for a long time! 
Now, take a break & munch on an ice cream sandwich. Num...
When everything is super duper dry, (OK, I'm impatient. Mine was mostly dry), you can cover the drainage hole with a few pebbles.
And then gather the curious neighborhood kids to help you with the rest. That's what I did. Well, I guess I didn't have to "gather" them. They just came over to see what I was up to. Even one skateboardin' boy said, "I want to paint some pots & fill 'em with flowers too!"
For some reason I had trouble deciding which plants to purchase for my cupcake planters. I wanted something that could be pruned to a roundish shape. I ended up finding this really thick, really lush plant called "Lobelia" Riviera Rose (at Fred Meyer). I also picked out some white Alysum for my smaller cupcake pot. I've never "pruned" them in a specific shape before, so we'll see how it goes!
After you plant your flowers, take some scissors or pruning shears & clip away any stragglers. I kinda butchered mine, but hopefully they'll continue to grow nice & thick.
My pots will sit outside. They'll eventually show the effects of the weather & daily watering. Definitely paint the inside of the pot as well as the outside. This will help keep the moisture from damaging your artwork. If you keep your pot out of direct weather elements this will help it to keep cuter for longer too.
Paint your dowels also. I painted mine with brown acrylic paint so it would remain inconspicuous in the pot-o-flowers. You'll be trimming the dowel to the correct size later.
And finally, paint the round wooden balls red. I spray painted mine. AND, I sealed them with a clear spray paint sealer.
Now you can work on the details of your pot, which you'll paint with brown acrylic stripes to resemble a cupcake liner.


Have a lovely day!