Cruel Valentine: An Interview with Chicago’s Own Community Chest

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Cruel Valentine: An Interview with Chicago’s Own Community Chest

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I recently had the pleasure of interviewing one of Michigan Burlesque Festivals 2014 Headliners and Chicago’s Own Community Chest, Miss Cruel Valentine. Check out her interview below and be sure to visit her website for additional photos, show dates and more! 

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HH: How did you get your stage name?

CV: Valentine is my given middle name, and it’s a family name that I wanted to honor through my art. My great grandfather’s name was Valentine. I actually had an extremely difficult time deciding what other word to combine Valentine with for my stage name, but the more I thought about it, the more I leaned toward incorporating juxtaposition. I decided on Cruel because I think the contrast between cruelty and the sweetness of a Valentine is interesting to think about. What also fascinates me is that when people address me, sometimes they call me Cruel, and sometimes they call me Valentine. When this happens at a show, I find that the name I get called more that evening often reflects the nature of my act that night. I guess each person gets to interpret which side of me they’re seeing at any given moment, which makes my performance life kind of an ongoing artistic social experiment.

Cruel Valentine HH: What inspired the act you performed at the Michigan Burlesque Festival?

CV: I’ve always loved the song Portions for Foxes, by Rilo Kiley, and I think that lyrically, it’s a piece that we can all relate to in one way or another. We all fall back into old habits, or seek comfort in behaviors that we know aren’t good. I’ve also been thinking a lot in recent months about the concept of news, both on a global scale and in one’s personal life. This year has been a rollercoaster for me personally. I’ve received amazing news and shared incredible experiences with my friends and colleagues, but have also received awful news in equal measure, and have found myself in some extremely challenging positions. I wanted to perform a piece that incorporated all of the joy and trepidation of these crazy cycles, as well as touching on sex, sexuality, and sensuality, which are so important one’s health, and are such a huge part of my both my personal and professional life. I also kind of wanted to put on a really sparkly strip show. I think I accomplished at least some of those things!

HH: What has been your favorite place to perform so far?

CV: It’s hard to narrow it down to a single place! I had an outstanding experience performing at several venues in Madrid, Spain last year, and just last night I assistant produced and performed in a stellar, ground-breaking show at the historic Michigan Theater in Ann Arbor, MI. Uhhhh, what else? I am in love with the Majestic Theater in Madison, WI, and the Mounds Theater in St. Paul, MN, and Metro in Chicago is always an amazing time. What makes a venue special, though, is not size, sight lines, or even reputation. It’s the connections you build, the family you shape while you’re there. I have had some not so great experiences in huge, beautiful theaters, and have made lifelong friends and given incredible shows in dark bars with sticky floors. I guess it’s all a matter of perspective, and who you choose to surround yourself with.

Cruel Valentine - Photo by Spilt Sugar

Cruel Valentine – Photo by Spilt Sugar

HH: How did you get started in Burlesque?

CV: I’ve been a singer, actor and dancer all my life. When I was studying musical theater performance in college, I learned quite a bit about burlesque and it’s role in shaping the modern musical theater format. I had never seen a show, but really wanted to. That winter, I saw an ad for a show called Gurlesque Burlesque being put on by the Sissy Butch Brothers. Margaret Cho was headlining. I had always admired her work, and was excited for the chance for two big firsts in one night. I was majorly impressed, to say the least. I decided that night that I needed to participate in this art form, and a few short months later, I went out for an audition and did just that! The show featured tons of local and international performers, some of whom I am now blessed enough to work with regularly. But wait! This is also a love story. Gurlesque Burlesque at the Vic in Chicago was also my first date with my partner of nearly 8 years, who is now my fiance. He produces and edits a lot of my music, and he’s been with me ever since the start of this crazy career of mine. You should check out his music here:

HH: What is your favorite costume piece?

CV: I have made and worn a lot of fun stuff over the years, but two that stand out are my Ikea outfit, which consists of a gartered corset and hoop skirt made entirely of Ikea bags, and my tauntaun head (from Star Wars, for those of you who don’t know what that means!) My dear friend, burlesque performance artist Red Rum ( helped me with the tauntaun creation. She is the best! The Ikea one was all me, though, because I am crazy.

HH: What is next for you?

CV: A NAP! I am so exhausted after stripping at a bachelorette party for my dear friends in Chicago, headlining the Michigan Burlesque Festival, then driving back to Chicago a few hours later to jump out of cake at a lesbian wedding, then preparing and coming back to Michigan for Pick a Card: A Burlesque Exploration of Tarot, that I don’t think I could handle anything else right now. Well, at least until Saturday, which is my next show in Chicago. I have lots of other big performance plans formulating, and am hoping to do some more modeling and photography for Zivity in the near future (

Visit Cruel Valentine’s website at 

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