Free Live Streaming: "Letters to Santa: The Second City That Never Sleeps" 24-Hour Improv and Music Benefit

If you’ve always wanted to go to a real Second City improv show in Chicago, this is as close as you’ll get -- and then some. The world-famous theater that spawned (and continues to spawn) all of our Saturday Night Live favorites is hosting its 11th annual “Letters to Santa: The Second City That Never Sleeps,” a 24-Hour Improv and Music Benefit. The improv performers stay up -- and perform -- for 24 straight hours to do this, peppered with musical and other guests. From what I’ve witnessed in past years, let’s just say that sleep deprivation can be an excellent muse -- and you get to watch it for free.

This year, Jeff Tweedy from Wilco is auctioning off a private show "for you and 29 of your closest friends,” Kim Deal from The Pixies is performing, guest improv performers include SNL’s Fred Armisen and Jason Sudeikis, and notorious recording engineer and food blogger Steve Albini will be interviewing Nate Silver. The live streaming is free, but the event is held annually to raise money for needy families in Chicago. To pitch in, you can donate to the worthy cause here.

Called “The Second City That Never Sleeps”, the event was started as a personal Christmas tradition by Albini’s wife, longtime Second City theater manager Heather Whinna. About 12 years ago she started giving gifts to needy families she picked from the Chicago post office “Letters to Santa” program. She would pick a few letters and just show up at their houses on Christmas and shower them with gifts and cash -- anonymously, never giving her name. In some cases, she would change their lives, like giving enough for a down payment on a car to a mother with a son who had a serious heart condition who had been taking the bus to the frequent hospital and medical appointments needed for his care. When she came back to visit with gifts two Christmases later, Whinna found a grateful, but grieving mother, who told her that without her help, her son would not have had the quality of life he was able to have in those precious last years. Moments like this, and the more light-hearted but just as life-changing moments like showing up to a house with few presents under the tree and giving every kid in it a laptop and the single mother $5000 in cash, were stories I would hear firsthand from Whinna in those early years and they would just shatter your heart.

What was different about Whinna’s gift was that instead of making a child’s Christmas brighter with a new toy, which is an infinitely noble endeavor, she is committed by her past experiences to making a bigger impact with gifts that just might change the trajectory of these families’ lives. So each year Whinna personally chooses about 15 letters -- as much as she can deliver in a day -- raises the money, and uses it to personally shop -- and wrap -- for each and every family member. She now enlists a crew that includes her husband, her father, and friends -- all of whom now swear they will never spend Christmas any other way.

Whinna grew the tradition from something she did on her own to an annual charity event at Second City where they match the money raised by the improv dollar for dollar. She still delivers the gifts, cash, and gift cards personally on Christmas Day and admits to absolutely being addicted to the rush of giving she gets by blowing these families’ minds. She now chooses the letters, most written by children, through the Onward Neighborhood House in Chicago.

If you suffer from insomnia, watching this show will be far more rewarding than scrolling through your friends’ insomnia-inspired Facebook status updates. It's definitely something you will never see anywhere else. It launches with Jeff Tweedy’s performance and auction on Tuesday night and ends tomorrow night with Tweedy’s son Spencer’s band The Blisters. In between is a lot of world-class improv, but personally, I’m setting my alarm for the 10:00 CST Steve Albini interview with Nate Silver.


  1. (*´ο`*)=3 はふぅん
    i-it was already *in progress* when this was posted.  it’s more than half-over while I write this 

  2. Can’t think of why I’d want to go to the one in Chicago rather than the one in Toronto, but to each their own, I suppose.

    What I /really/ want to do is go back in time and watch an episode of SCTV being filmed.

  3. Two kids from the same poverty-blighted street write letters to Santa. A rich lady turns up outside one of their doors with $10,000 and a box of laptops. The other kid gets nothing.
    Is this type of philanthropy actually beneficial? It is satisfying for the person doing the giving, and for the families receiving the gifts. But wouldn’t anyone with a broad knowledge of urban social problems prefer that you gave your money to a charity or foundation that can tackle the problem on a wider scale?It just seems…arbitrary to me. Life changing chances for a select few of the poor, based on the personal whims and sympathies of the rich. I’m skeptical.

    1.  Do what you can with what you have. As the article says, she manages a theatre, and Albini’s probably not doing too badly, but ‘The Rich? The article also says, they’re running a benefit to pay for it. ‘The Rich’ could solve the problem at the drop of a fucking hat and still be rich

    2. I’ll give a little of the receiver side perspective. I’m not poor and, having grown up living hand to mouth I feel like I do know the difference and am always thankful for what I have; however, one year at Christmas things were extra tight for me. A lady I knew, kind of a friend but not a close one, gave me $200 in her Christmas card that year. It made my year. It was so unexpected and so sweet. I never forgot it.

      This year I am ahead for, like, the first time ever at Christmas and so I am sending on $200 to my sister as a little pay-it-forward gift – and helping my brother pay for a hotel room and sprinkling little extra gifts around to friends I don’t normally gift.When times are hard and someone takes the time to do something special for you, especially someone where the money doesn’t have strings attached, it can change your outlook in a wonderful way.

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