My Way is a “Crap Song”: Reflections on Regret

Say what? I was out for a jog this week and I had to stop, […]

Howie Espenshied / 12.12.14

castSay what? I was out for a jog this week and I had to stop, take out my earbuds to squeegee out my ears with my fingers, hit rewind, and hear that again. Did Ira Glass just disparage Frank Sinatra? Ira Glass is the creator and executive producer of NPR’s weekly podcast “This American Life”. I was made privy to this can’t-miss weekly series by this Mockingbird post a while back, and I’ve been riveted every week since.

Each week’s podcast features 3 segments of real life Americana stories that are centered on a basic (and usually innocuous) theme. The December 5, 2014 podcast “Regrets, I’ve Had a Few” is of course titled after the Sinatra classic. Glass introduces the episode (featuring 3 unique interviews/stories about “regret”) by calling Sinatra’s classic a “crap song”. We really shouldn’t be surprised. Glass appeared on the Tonight Show with Jimmy Fallon in September and admitted to calling William Shakespeare a “lousy storyteller”. He didn’t elaborate with Fallon on why he believes that, but his point about the Sinatra classic centered on one particular, well known line – “Regrets, I’ve had a few, but then again, too few to mention.

Glass reads that line aloud on the podcast and responds incredulously, “Really, you’ve had TOO FEW regrets to mention?…well, the rest of us aren’t likely to relate”. I had never really pondered that line in the song before, but wow, Glass has a point.

I unwittingly double-dipped on regret this week. My wife and I watched the HBO miniseries “Olive Kitteridge” on our DVR. It’s tremendous (right up there with “Temple Grandin” among the best HBO miniseries dramas). Frances McDormand plays the titular character – a small town high school English teacher who struggles with depression and thoughts of suicide, especially as she reflects back on her life and how she verbally abused and mistreated her husband and son for 25+ years. It’s a fairly sobering and dour four hours of TV, but it ends wonderfully in the way it depicts the hope than can emerge when regret gives way to acceptance.


It has been hard not to reflect on regret in my own life after that pop culture double whammy. As I think through all of the roles I’ve played over the years (father, son, husband, friend, sales guy, minister, referee, coach, etc.) each are marked with moments that make me cringe. Regrets, I’ve had a few, but then again, way more than a few. At the end of the day though, I’ve come to believe that regret is the opposite of hope. If regret is looking back remorsefully at our failings, hope is looking forward to the assurance that it all will be made up for – that every wrong will come undone, and all the sad things come untrue, as Tolkien wrote. I find myself at a place in my life where I can’t imagine not having the hope of the Gospel – the ultimate place to take regret to.

There’s a sense in which we can all look back over our lives and sing “I did it my way”. As a triumphant anthem, Ira’s right: it is indeed a “crap song”. But I can see it working as a lament. Too bad, though, that laments don’t become iconic very often.