Is there a "right" plant to grow in a concrete Pot?

Plant i a smaller pot with drainage holes and place inside of them.

I would remove any paint that is flaking and repaint with a white cement paint (on the outside only) if you don't like the distressed look. Personally I would just clean them with a wire brush to remove any dirt/moss and leave them with the traces of paint. Any partial shade plant will work in the pot, if you keep them with the same finish or paint them white I would be tempted to add bright flowers, (I,e. Begonias or New Guinea inpatients) something that trails (baccopa, creeping Jenny, trailing lobelia) something fairly tall and something with a textured/feathery leaf or coloured leaf (coleus comes in various colours) you could do each pot with a different colour scheme but keep the greenery/trailing/textured leaf elements the same for unity

I do the same thing - good drainage is critical to plant health. It also makes it easier if you want to move the plant. A concrete container filled with dirt is heavy!

I don't know how to clean the pots, but you could plant a large variety of plants as long as you supple drainage in the bottom of the pots. I have tomatoes growing in containers for the first time this summer and they are doing great. Drainage is one of the most important ingredients in container planting. I used just plain rocks, average about 1" or more to cover the bottom of my containers. Hope this helps.

The type of drainage I am talking about allows excess water to stand without the roots being damaged from being in the water.

I have several of the cement pots. Depending on where you live Water may not be an issue. My Cement Pots seem to Evaporate the excessive water really well. I would Not drill any weep Holes in the Pots as the Cement is Very Old . Asparagus Fern in my Pots work really nice.

As for the Color... a Soft Gray with Light touching of White in the area's of the Cement flowers or Creases make the Pots look Very Elegant. An almost dry paint brush or small rag works really well in these area's. Remember to use an Outdoor Paint.

I love the weathered look - I'd leave them like they are - I have great luck with Hens and chicks (succulents) growing in mine year round - they require little care and droop over the edges

I would not drill the cement pots but rather put small pebbles in the bottom and place plants in plastic pots on the stones. That way the plants have some drainage. I too love the asparagus fern. Also, the little petunias that vine would look great. I'd place the large pots behind the small pots.