Album Review – Olds Sleeper’s ‘I Will Follow You to Jail’

September 2, 2011 - By Trigger  //  Reviews  //  17 Comments

Unless you frequent a few small music circles in the underground world, you may have never heard of the artist Olds Sleeper, but that doesn’t diminish the argument one can make for him being one of the best songwriters of our generation.

Of course, saying anyone is the “best” of anything is always disputable, but numbers are not, and by the numbers, Olds is indisputably one of the most prolific songwriters out there, especially taking into consideration he’s also the singer, picker, performer, engineer, publicist, and label.

Some songwriters, trying to explain the dedicated nature of songwriting, say that songs are like children. Well if that is the case, Olds Sleeper has shagged more trim than an NFL wide receiver, and has baby mammas and kiddos with his nose spread all over town like a bad rash. If you don’t like an Olds Sleeper song or project, just wait a month or two; the next one will be coming around soon enough. It’s to a point where Olds’ proliferation is an element of the music itself. Good songs are elevated to greatness by the wanton “write it, record it, and move on” nature he approaches music with. And then what happens with these songs? They’re disseminated through email or on the internet, cheap or free. Come and get ‘em.

It is said the systemically-morose life the modern American male leads is one of quiet desperation. Olds gives that quiet desperation a voice, and a vehicle in I Will Follow You To Jail. Towns and women, and unresolvable circumstances and sins paint a bitingly authentic picture of a man at wit’s end. It is a soundtrack for the American anti-hero, making you fall in love with the villain, cheer on bad male middle-aged behavior, and see the beauty in otherwise ugly things. . . . . and then Olds plays a bad ass banjo instrumental.

And despite Olds’ seemingly-fleeting attention for his songs, every one of them has some element of brilliance; a quality other songwriters might labor on a song for months trying to obtain or capture, to no avail. But with Olds, this element of brilliance is where a song must begin. And then like with all great albums, there is a universal theme bridging all the songs together.

The music is endearingly sloppy, though at no point rushed, incomplete, or careless. There’s even an attention to detail, in ambient layers he adds to the music, and the subtle inflections in his voice. Olds’ lyrics imbibe an awesome sense of character that help personalize the truths of his message to where it sticks to your bones, all while making sure there’s humor and simple appeal at the song’s core first. The authenticity goes without saying. His use of tone, instrumentation, and effects is always appropriate. Though another spellbinding element to Olds Sleeper is his diversity of style (I’ve heard him do things that could be characterized as techno or industrial) I will Follow You To Jail is solidly a dirty roots-based album.

The desperate mood is set with “If I Had A Bottle” and evolves to self-righteousness bravado in one of the albums standout tracks “I’m The Devil”. The other must have tracks are the heart-wrenchingly real “This Town” and the disturbingly-funny and soulful “(Buddy Holly) Paranoia Blues”. These are balanced by two good love songs “Should Have Turned” and “Much Too Smart”, and three solid banjo tracks. And what would you pay for all of this? Well, the asking price is nothing, so you now have no excuse to not go an check Olds Sleeper out for yourself. All I ask is that if you like it, you tell a friend.

Two guns up!

Download I Will Follow You To Jail for FREE on Bandcamp

17 Comments to “Album Review – Olds Sleeper’s ‘I Will Follow You to Jail’”

  • Great review, Trigger. If you want stripped-down, bare-bones, DIY dirty roots music, look no further than Olds Sleeper. With every album he seems to fine tune his “process” (if there is one), and this album is no different. Some of his finest work yet. And now … I wait for the next one.


  • Thanks for hipping me to this guy.I am intrigued and excited to discover a new voice.


  • I have been listening to Olds Sleeper for sometime now I am haunted by his creativity. Often times I have found myself relying on his work as I do mine. His music has been on in my shop for countless hours while I am working. I recently told Brian Burnette I carved the neck of his guitar while playing June and Gemini (repeatedly).

    Olds builds his music in layers that continue to take me places I want to go. Electric, acoustic, guitar, banjo rocks clanged together I think he can play anything. Add to that he’s one of the best story tellers of all time. I have no idea why he is not famous. That is until you think about how the music industry and mainstream music works.

    This is another gift that Olds has given us download it, and if you are not familiar with his music check out his catalog. Hear for yourself why Olds is special to so many of us.

    Jim Mitchell


  • thanks a lot trig,…it means a lot to me, sincerely.i think there is another story here too…people like rev. nix and bj christy willing to play artists who dont often get opportunity to share what they are doing….its cool. .and of course, scm for the courage to support those dudes, too. anybody who actually goes and listens what im working on: thank you.


    • damn good stuff olds. i’ll be lookin for more.


  • Thanks olds, great songs, heart and soul. Appreciate the gift. And Triggerman don’t know how you keep findin these guys but I’m glad you do. Makes it a little less lonely out here in the cold.


    • Excellent cover and album man. Getting something this good for free was a real treat. Loving it!


  • Thanks Triggerman… and of course Olds. This is fantastic!


  • Wow! Like the best treasures, it sometimes takes awhile to uncover and admire. Anything that gets me inspired is 100% treasure and so’s that banjo. Now where’s my paper and pen?

    Great blog Triggerman.


  • Great album Olds, you deserve every bit of praise and more! Great sounds and songwriting.


  • Great review Trigger! I have got to say knowing Olds on a personal level is a privilege. He is one of the most down to earth guys I know. And I thank Rev. Nix every day for that. I have all of Olds’ albums in heavy rotation around here. And to watch him come up with songs on the top of his head, there is a greatness there that I hope you realize, Olds. Can’t wait for the next, album. I know you will blow us away with that too.


  • Man, this is f-in awesome music! Olds is a true troubadour! Thanks for this review, Trig!


  • WOW great review! So cool, i freakn love Olds music. Seeing a review on here makes me smile so wide! He is doing something new and fresh with singer song writing. Thats what puts Olds in his own handmade only him Folk category. Take Will Taylor another GREAT Folk artist true to Folk nothing wrong with that i love Willie T a shit ton! But Olds opens up a new direction in Folk only he does as far as i know… Its only getting better. If you can find a download that cost BUY IT because it will change your life. If your in this small inner circle you sure know about the Olds Sleeper challenge if your not go get all of his stuff and listen to him all day nothing else it never gets old because its fresh and new. I have over 100 Olds songs in my library and am always looking for more….


  • One thing missing from Muddy Roots Music Fest this year for me was Olds Sleeper. I had so hoped to sit around a camp fire and listen to him sing. I still maintain my girlie crush on him and it only gets worse when I hear these new tunes.


  • Cheers Trigger,

    What would I be without you regarding discovering new and great music here in Netherlands (Europe)…..
    Many Thanks for your site.. and ranter


  • Wow, what a treasure, loving his sound. Hauntingly beautiful. When I clicked on the link I hadn’t yet read that Malfangled Dog Records was Olds own label and was going to comment on the poignant tag line “Lo Fi folk from the hills, shade and streams of Pennsylvania”. That condures up such a beautiful image. Definitely an album to add to my list. Love the cover art work too.


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