A Picture of Boston: Lenny and the Piss Poor Boys
By: Ryan O'Connor
Tags: Art, Boston, Magazine, Review, Music

A Picture of Boston: Lenny and the Piss Poor Boys

Lenny Lashley’s underappreciated country album is one of Boston’s most poignant artistic expressions

Lenny Lashley is one of Boston punks most beloved figures, even if a lot of his outings have flown under the radar in comparison to other artists from the area. He first popped up on the scene in the mid 90s as the leader of Darkbuster, Boston’s hard-drinking party band whose lyrics consisted of drinking beer, fighting, making grave mistakes, waking up hungover and doing it all again. The perfect soundtrack to any New Englanders weekend. What drove it all home for the listener was how Lenny’s lyricism always painted this debauchery in a more cynical way, there was always some regret or consequence to the fun being had. Time was being wasted and life was passing us all by as we indulged ourselves in the drink, the drug and the lust.

After Darkbuster disbanded for the first time Lenny continued his tales of hard luck and regret for the next two decades and his storytelling has only ripened with age. He’s carried his musical skills into other bands as well, notably playing rhythm guitar in fellow Boston rockers the Street Dogs which he played in for seven years before departing in early 2020.

Lenny’s solo career however is where he truly cemented his status as a local hero amongst the Boston music scene. His current solo outing is Lenny Lashely’s Gang of One which is where I first came across Lenny’s music in 2014 when I saw him and his band open up for Flogging Molly at the House of Blues. It wasn’t until a couple years later that I truly delved into Lenny’s back catalogue and found Darkbuster and later fell in love with his first solo outing: Lenny and the Piss Poor Boys and their self-titled album.

This album took a giant leap from Lenny’s punk rock roots with Darkbuster as Lenny firmly planted his boots into the country/folk territory which is a rarity in the east coast… maybe not necessarily but it’s mostly music that you hear played in bars and tip the guy playing as you stumble outside to puke your guts out on the sidewalk. Boston’s a rock n’ roll type of crowd, that’s what sells here at least but Lenny chose to stick to a style of music that provided the perfect backing to his hard luck tales of growing up on the wrong side of the tracks, which is the title of the first song on the album. In all honesty the album is one of the most aesthetically pleasing to the authentic Bostonian culture which is disappearing due to gentrification and it reflects an understanding of that world better than in the movies.

Lenny begins the albums first song “Wrong Side of the Tracks” with the line “In an old steel town they’re closing factories down/ Mom and Dad split up cuz he’s a bastard” and from there you can instantly picture where the albums content will come from. This isn’t just laughing off the pain and drinking it away for good times anymore, this is downright upsetting and hopeless from the start. What’s worse is this is the reality for a lot of people in the Greater Boston area and its possible that many of the listeners of this album are drawn to it because of the relatability of the lyrical content.

Lenny fits into this record better than his previous punk records, hearing his vocals and instrumental work on this record sounds like a man who has truly worn in the work boots he bought years prior. His voice crackles across the tranquil country-esque music, it has a tinge that releases an odor of Jim Beam and cigarettes and it fits the sound so well as he croons his hard tales of dead friends, hangovers spurred by nights of debauchery and cradled with severe loneliness. It’s a hard voice that gives Tom Waits’ grave voice a run for its money, it scratches your ears as you listen, you can almost feel his unkempt beard at your ears as the smoothness of the slide guitars ease you into the affair. His voice makes him sound older than he is on the record, to never have met the man I would have pictured him to be in his 50s recording the album, but he was really in his early thirties.

The third song on the album pays homage to a long gone Boston landmark the Cambridgeport Saloon on Mass. Ave in Cambridge, a picture of which is featured on the albums black and white cover. The dive bar was a seemingly unsavory place for the yuppies in the city but a haven for the locals as you could find yourself there at an ungodly hour of the night grabbing a few beers at less than $2 bucks a pop. Places like this are a godsend in the city of Boston and they’re all but disappearing in favor of cute hipster hangout spots to make the yuppies feel cozy. Lenny’s song pays homage to the stories people most likely told, or he probably lived through himself, of their weeks leading up to them sitting at the barstool and you can imagine they aren’t enjoyable.

The most depressing part of the song in my opinion is the verse “I fell down and didn’t get up, they took me away/ I’ll be back tomorrow night and start it up again” because we all know this one is absolutely true. No matter how bad of a situation you’d find yourself in, you’ll never learn the lesson that’s slapping you in the face. Perhaps you’ve already learned it but it’s just too late.

The most appealing piece of this album is how much soul it contains, it’s truly the sound of a man bearing himself as any busker found at a pub would in order to set the mood for the patrons. Lenny’s lived a hard life, no doubt about that but he’s come out on the other side to tell the tale but when this album came out in 2005 I’m not sure he had made it out of his own personal hell just yet and that to me brings out such feeling in the record.

The music is tinged with the sounds of outlaw country and maybe some folk music reminiscent of Bob Dylan. The slide guitars ooze with the peaceful rhythms, there are also some rockabilly songs such as the track “Whiskey and Water” which is one of the many standouts. Lenny speaks to and for a community in the Greater Boston Area that is largely being ignored and suppressed these days as gentrification has all but forced them out of the city. Despite the area’s penchant for hard rocking music it’s Lenny’s easy going country soul that can carry us all through our days of hard working and unbearable realities that we all are struggling to get through, often turning to substances to ignore. The album still maintains that punk attitude that Lenny had from his Darkbuster days and that’s what gives this album the crossover appeal to fans of his earlier output, he’s maintained his integrity throughout his career. There are many artists in the Boston area that have tackled this sound but Lenny’s first solo album in particular stands out amongst them all, there’s a certain magic in the sound of this album and I wish he did more as Lenny And The Piss Poor Boys but just hearing from Lenny is good enough.

This album sinks under a lot of people’s radars I find and that’s a shame because I think it would speak to a lot of people. It was on streaming services for awhile which was where I first discovered it but it recently disappeared from Spotify and is nowhere else to be found. This was a devastating loss and I can only hope in writing this that it can somehow be put back up, it’s carried me through a lot of hard times. We all find ourselves in hard times and a lot of music can reach out to us and carry us through them, this is one of those albums for me and I sincerely doubt I’m alone in this. I’ll always keep carrying on hoping to live to see myself live out the line Lenny sang on my favorite track “Beat On The Brat,” “I’m thirty-something and I don’t feel old/ Still listening to punk rock still like my beers cold/ I got the best gal I’ve ever seen and I can’t wait till we hear her favorite song again.” Someday we’ll all make it through.