Wednesday, January 5, 2011

Roselyn Bakery Smiley Face Cookies

In my last post, I shared many of the details from my 1st Annual Cookie Party. (Do you like the reference to the "1st" cookie party - is it obvious enough that I plan to do this again??) Today, I'd like to share the cookies I made for the swap, as they are most definitely my favorite cookie of-all-time.

When I think of exchanging cookies with 20 or so other women, aside from drooling in anticipation, I immediately think about what I can bring to the table (pun most definitely intended). It's no secret that I have an insatiable sweet tooth. I eat chocolate every single day and almost never turn down a cookie. I'm the type of person who loves to try new recipes, especially sweet ones, but when it came to this party, I wanted to go with something I knew could never fail me. And that my friends is...

Roselyn Bakery's Smiley Face Cookies! These cookies are hands down my favorite cookie of all time and one of the reasons I obsess about them is the history I have with the cookie. 

From what I learned from Mr. Internet, Roselyn Bakery first opened its doors in 1943 in Indianapolis, Indiana and over the course of several decades, opened several additional bakeries in the Indianapolis area. (The bakery subsequently shut down in the 1990s due to rat feces found in the main baking facility...)
(Note on photo: since the bakeries closed prior to the digital age, I'm afraid there are very few images available of the old bakeries. Such a shame! I've yet to find a picture of the Smiley Face cookies or even an image of their infamous pink boxes!)

One of the warmest memories of my childhood would have to be Roselyn's Smiley Face cookies. They were HUGE (probably 5" wide) ovals, colored yellow, with a chocolate buttercream smiley face piped on. The bakery I frequented was in downtown Franklin, IN where I grew up. We lived just outside of town, close enough for me to ride my bike to snatch a $.99 cookie in the early 1990s. I can remember so vividly scraping up enough change to buy a cookie (or two) and to this day I remember the absolute joy in eating the cookie. I barely made it home without half the cookie gone, but I do remember trying to muster enough constraint to save at least half the cookie for "later". (Do you know how difficult it is for an 8 year old to savor anything?) Of course my mom (from whom I acquired such a lethal sweet tooth!) would often purchase a Smiley Face cookies for me - but there's just something about being a kid and being able to satisfy a craving of this magnitude on your own dime!

When I say, "favorite cookie of all time", I truly mean it. I couldn't tell you what I enjoy more - the childhood memories or the actual taste of the cookie. I'm fairly certain the taste is enhanced by the memories, but I'm sure I'd still love the cookies even without them. There is nothing else out there like it - and believe me, I've looked (and looked, and looked, and looked). The cookie is buttery and dense like a shortbread cookie - but with much more flavor. It's rich and melts in your mouth. It's even good enough to stand on its own. That said... it's actually the icing that makes this cookie so spectacular.

Just after sending the e-vite for the Cookie Swap, I promptly RSVP'd with my cookie of choice... my favorite childhood cookie... the Rosalyn Bakery Smiley Face cookie. (However, since the theme of the party was "snow" I shaped my cookies into snowflakes.)
Here is my messy kitchen while attempting to ice my snowflake cookies. The icing for this recipe is quite finicky and rather high maintenance (hence, the reason I typically only make this cookie once or twice per year). This icing is comprised of three varieties of sugar - granulated, powdered, and syrup. (And if you count sugar that has been boiled, then there are four varieties.) The idea is to "spoon" the icing over the cookies and allow gravity to pull the icing around every edge.The ooey, gooey-ness of the icing spills over all sides of the delectable cookies (and if you're lucky, some will magically appear on the bottom of the cookie as well). However... the icing becomes very thick very quickly and it's actually quite difficult to tell how much powdered sugar is actually adequate. (Or maybe that's just my excuse?) I'm also fairly certain the amount of time you are supposed to boil the sugar has an impact on the harden period, but the recipe is so vague it will take some time for me to figure that out. Anyway, with a bit of finagling, I had my cookies iced. For the small snowflakes, I scooped the icing into a pastry bag and whisked it back and forth over the cookies to create the stripped look. 
  Seriously, I've never experienced icing like this before.

Side-note-to-self: don't leave pastry bag with ooey-gooey icing near the edge of the counter, as your mini-baker will be standing by to lick up your mess! And he won't stop just because that sticky icing is dripping all over his face - he'll stand there any way and the require a bath in the middle of your cookie icing experience and therefore threaten the outcome of your cookie party contribution! Whew. I said it.

Anyway... Several years ago, I decided to scour the internet for the recipe for my beloved Smiley Face cookies after a major let down from a local grocery store that carries "Roselyn" recipe items. As luck would have it, I found a recipe that is so dangerously close to the original (as my memory would serve, any way) that I can make these cookies and immediately be taken back to my childhood.

And here you have it...


1 cup butter
1 1/4 cups Crisco shortening
1 1/2 cup granulated sugar
2 tsp salt
1 1/2 tsp vanilla
1 egg white
4 egg yolks
5 1/4 cup all purpose flour
Dipping Icing (recipe follows)

Cream together butter, shortening, sugar, salt and vanilla. Mix only until smooth. Add egg white and egg yolks. Blend into butter mixture. Add flour. Mix until dough is stiff and waxy. Refrigerate dough until firm.

Preheat oven to 350 degrees F.

Roll out dough between two sheets of wax paper. Cut into rounds. Place on lightly greased baking sheets. 
Bake at 350 for 13 minutes. Let cool and place on wire rack to cool completely. 
Spoon dipping icing over each cookie. Decorate as desired.

Makes 4 dozen cookies


1 cup granulated sugar
3/4 cup water
6 - 7 cups powdered sugar, divided use
1 cup vegetable oil
3/4 cup light corn syrup
1 1/2 tsp vanilla
yellow food coloring

Combine granulated sugar, water, and 1/2 cup powdered sugar to saucepan. Bring to rolling boil. Remove pan from heat and set aside to cool.

Place vegetable oil and corn syrup in a mixing bowl. Stir in the cooled mixture. Add remaining powdered sugar and mix until all lumps are gone. Add vanilla while mixing. Mix together well. Stir in yellow food coloring as needed for a smiley face color. Pipe chocolate buttercream icing on (or not) as you wish.


  1. I stumbled on your site and I'm so glad, it took me back to my childhood. I moved from Indianapolis when I was 7 and for the last 20yrs have missed these cookies! My kids thought I was nuts for loving a cookie so much but they soon found out why when we made them, they are already planning a batch for valentines day. I also had icing issues however, it was thick and just sat on the cookie and never hardend right, the taste was there just not the thickness so if you have any updates on the recipe let me know so I can try again!

  2. Hi Jamie! So glad to hear I'm not the only one obsessed with these cookies from so long ago!

    I actually updated the recipe above with what I think is the appropriate amount of powdered sugar. The trick is the then leave them to set over night. If you're anything like me, it's VERY difficult to wait that long - but I think you'll be happier with the result. Also, if you still find the icing too think to naturally drip down the sides of the cookie, give it a little help with a spoon. I've found that you can heat this icing in the microwave as well and it doesn't alter the chemistry enough to change the outcome. My last tip would be to use a simple shape cookie - like a circle. However, I would think a heart would work as well. Enjoy your Valentine's version!!

    Good luck!

    1. Thank you for sharing this recipe! I too am I fan of thr smiley face cookies. I looked forward to buying them for my girls when I moved back to Indianapolis only to find the bakery closed. I have never baked cookies before but for this cookie,I will try.

      Thanks again

  3. I just came across your site after looking for the recipe for the icing for the Roselyn smiley face cookies. I grew up in Indy, and I remember stopping with my mom on the way to the babysitter at Roselyn bakery on special mornings--she'd get some coffee cake, and I'd ALWAYS pick the smiley face cookie.
    We actually have the Roselyn bakery cookbook which has this recipe in it, but we've had a really hard time with the icing as well. However, our problem has been that the oil does not properly mix in with the sugars, so it separates out and sits on top. This doesn't affect the taste of the cookies, but it is kind of gross, because the cookie "sweats"--the oil works its way out of the icing and just sits on top. You can wipe them off with a papertowel, but eventually more will "sweat" out. The weird thing is, we had made these cookies 3 or 4 times without having this problem, but the last 3 times, it has done this. Any idea what we could be doing wrong?

  4. Do you have the recipe for the buttermilk cookies? Brownies....chocolate chip cookies???? The cookbook is too expensive for me!

  5. Sorry - I do not have the cookbook but a lot of the recipes are out there in cyber space!

  6. OMG, so glad to find this...your description was spot on from what I remember too. I actually just wrote Roselyn Recipes for the recipe (slim chance but I wanted to try). I'll share should they give the secret. I'm going to use your recipe to make as close to the original as possible. Any idea as to what icing should be used for the chocolate eyes and smile?

    Take care!

  7. Hi Courtney - I've used a simple chocolate buttercream for the smile before. If you use my buttercream recipe, simply add cocoa flavor to your desired chocolate-strength.

    Have you had the chance to make this recipe yet?

  8. Thanks for the recipe! A smiley face cookie was always on the list of things to do while visiting my grandparents in Indiana! I can't wait to try these :-D

  9. Try the libraries in Indy, about 5 years ago I found the Roselyn cookbook available to be checked out...had tons of fun making all the recipes.

  10. I have the recipe book & you're pretty close on the amounts. They list the following:

    3/4 C water
    1 C granulated sugar
    9 C Powdered Sugar
    1 C Vegetable Oil
    3/4 C Light Corn syrup
    1 1/2 T Vanilla

    They divide out 1/2 C powdered sugar to add to the water & granulated sugar & bring to a boil.

    Hope that helps!

    1. Thanks for your post. I specifically lowered the amount of powdered sugar because I think that 9 cups is too much.

  11. Oh my goodness...I am sooo excited that I found this site!!! I too am from Indianapolis and I lived right down the street from Roselyn Bakery. I would walk there all the time. I think I loved everything at the bakery. I cannot wait to get my cookbook in the mail!!!

  12. I have the recipe book if any of you still need one of the recipes. Just let me know!

  13. I'd love to have the Buttermilk Cookie & Sugar Cookie recipes. THANKS!!!

  14. Is there a recipe for their Canasta Cake in the book? My mother-in-law loved that cake when the stores were around here in Indianapolis.

  15. I grew up in Lansing, Il and we had a bakery named Village Bakery that made these Smiley Face cookies. I loved them, and at 52 they still remain a vivid GREAT MEMORY from childhood.

    I now bake at home for a job and deliver all over my area. I have been thinking about introducing the South to my favorite sweet as a child. I came across this site a few months ago while searching for the recipe.

    Tomorrow is my day to finally try these cookies. After I read all the comments, I am praying they turn out like I remember them as a kid. I can't wait.

    1. How did these turn out for you? As good as you remember?

  16. Thank you for posting this. I am gonna try this soon. I also grew up eating these cookies and I love them. in the late 90's when I grew up and moved out on my own i would always to go and get these from the bakery surplus store I think I paid $2 for 8. I would always pick up a couple packages of these and a package of brownies. this is the only thing I can think of where I can actually say my kids don't know how good I had it lol.

  17. I also grew up in Lansing, IL & ate these cookies all through the 70's as a kid. I missed them and now I am a baker. I am so excited to be making these in my kitchen right now. I hope they turn back the hands of time!

  18. Oh my goodness!! Everything you described above was me when I was little. We lived a few blocks from the Roselyn Bakery on the south side of Indy (which looks identical to the pic you have posted...background and all). I can still remember me and my little brother getting on our bikes and heading there with piggy banks and all. These cookies were and are still my absolute favorite! I've never found a cookie that I loved as much as these and I'm soo glad I found this. Now, since I've made these, I can't get enough of them. Not only do I love em but my kids love them just as much. You have no idea how hard it is to give up the last couple of cookies so the kids can have them :) I even bribed my brother with a batch in exchange for painting my front porch! Thanks for the awesome recipe and fantastic memories these brought back.

  19. Made the cookies with just normal royal icing, as I had no corn syrup, and they were great! I'm wondering if you or anyone have tried putting lemon juice in the cookie dough to add a little more flavor? If so, how did it turn out? I like that extra flavor with this type of cookie

  20. Not sure if this is still an active blog. I have been trying to make the buttermilk jumbles and in my search came across this... some saturday here soon i may try my hand at these. I adored the smiley face cookies and bought them multiple times a week. I am always looking for a similar cookie but none have come close to my memory of the smiley face cookie! Thanks for sharing...

  21. Not sure if this is still an active blog. I have been trying to make the buttermilk jumbles and in my search came across this... some saturday here soon i may try my hand at these. I adored the smiley face cookies and bought them multiple times a week. I am always looking for a similar cookie but none have come close to my memory of the smiley face cookie! Thanks for sharing...

  22. Does anyone remember the ghostie cookies? I remember liking them much more than the smiley face but I'm pretty sure out was the same icing. Perhaps food coloring made the difference?

  23. Not sure if this is still active. I've been looking for this recipe. Our local bakery closed that used to make these. Thanks for the recipe

  24. Thanks! Greenwood, Indiana now living in Texas. These smiley cookies were my special birthday treat in childhood. Now I'm a baker and going to try to recreate.

  25. Is this the same icing that they would use at Easter time on the little egg cakes? It hardens up?


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