Michael Penn on Brightening Up a New ‘Sweet Relief’ Charity Album With Songs From the Great Depression: ‘It’s a Mirror Image of Where We Are Now’

It doesn’t have to be a Great Depression — yet — for musicians who lack health care to get downtrodden about their prospects. To that end, the Sweet Relief charity has put together a new compilation album, “Sweet Relief — We Can Help,” which features choice covers from artists like Lucinda Williams, Richard Thompson and Blake Mills. But only one singer is heard from twice in the collection, and it’s someone whose name hasn’t appeared on a lot of records lately: Michael Penn.

Penn’s two contributions to this philanthropic effort are classic prewar anthems that spoke to how many members of the middle class were falling into economic ruin in the chaos in the late ’20s and early ’30s — “Brother, Can You Spare a Dime?” and “Hallelujah! I’m a Bum,” the latter of which also includes a duet part from Aimee Mann.

His two tracks will add to the collective that will throw more than a few dimes the way of the struggling musicians that Sweet Relief supports. He’s been a supporter for a while. “In fact, my first tour” — soon after his breakout single, 1989’s “No Myth,” was all over the radio — “I had Victoria Williams on the road with me, and it was just a blast. It was around that time that she was first dealing with her MS diagnosis and thinking about forming Sweet Relief.”

These two songs were actually first recorded more than a decade ago, with the intention of being included in a previous Sweet Relief compilation. It was determined that they didn’t fit the mood then, conceptually. But now, with not just musicians but the wider world worried about recession (or worse?), these Depression anthems felt practically ripe on the vine. While “Sweet Relief — We Can Help” came out in an exclusive vinyl double-LP edition for Record Store Day in April, the official digital release of the album waited until this weekend. (Scroll down for a full track list.)

Penn’s contributions really drive the wayback machine hard, but “both these songs are so applicable now because they both come out of historical situations that are analogous to where we’re headed,” says Penn. “If I was going to do any song at all, I knew ‘Brother, Can You Spare a Dime’ was the one I wanted to do, because Yip Harburg is one of my favorite lyricists of all time.” (Harburg also co-wrote “Over the Rainbow” and the other “Wizard of Oz” songs as well as “Brother.”)

“And then with ‘Hallelujah! I’m a Bum,’ I was a little worried that people would not get the sarcasm of it — because it really is a mirror image of where we are now. It was written around the time when the oligarchs and the quote-unquote ‘titans of industry’ building the railroads were in control in the late 1800s. And it’s the same as fucking Elon Musk! I mean, the guys who ran the tracks across the nation were the same kinds of crazy oligarchs that we have now.”

With “Brother, Can You Spare a Dime,” he was particularly taken with a quote he found of Yip Harburg’s, from later in the famed lyricist’s life, when he was recalling his Great Depression anthem. Penn pulls it up on his computer and recites it: “I grew up when America had a dream, and its people, a hope. Whether we were struggling against the shackles of slavery or the shackles of scarcity, the hope was there. In 1930, the dream collapsed. The system fell apart. The people were not angry. They were not in revolt. This was a good country on its way to greatness. It had given our immigrant parents more freedom, more education, more opportunity than they had ever known. What happened? We were baffled, bewildered… The man in this song is not a self-pitying breast-beater, begging for a handout, but a man proud of what his hands had contributed to the wealth of the country. And he was now, for the first time, questioning the emptiness of those hands.” Penn was taken by the timeliness of those words: “I mean, it’s just so perfect in that way.”

With “Hallelujah! I’m a Bum,” as he says, getting across the irony was paramount. “Bill Hein reminded me that the exclamation point was an important part of the title.” Of the historical sarcasm, he notes, “Listen, sometimes it’s the only thing we can count on.”

Is Penn a student of socioeconomic songs from the 1920s and ’30s? He laughs at that question.

“No, I’m not. I’m certainly not a student of the ins and outs of union songs from the 1930s.” And “Hallelujah” definitely counted as that — enough so for it to be interpolated as an instrumental in-joke in the score of a Charlie Chaplin sound picture. “It became the official anthem of the International Workers of the World at some point,” Penn notes, “and a snippet of it shows up in ‘Modern Times,’ when Chaplin is mistaken for a union protestor,when he picks up a flag off the back of the truck.”

But, he says, “It’s just stuff I have sort of always thought about. My last record, God help me, was 20 years ago, but it was a record set in sort of the post-World War II world. It was relationship songs in the context of a post-World War II America where they were starting to figure out how to dismantle the New Deal. And in fact, when I put that record out, I had this very elaborate website where you could watch these old Encyclopedia Britannica documentary films from the ‘50s about fascism. Because it was clear that that was the model that was (coming).

“Remember that phrase where somebody was saying that ‘you people live in a reality-based community’? That was the clue of: This is where they’re going. They think that they can completely change reality for us — that they can fill us with propaganda and change the way we perceive our environments, and it was obvious that that’s where shit was heading. So those kinds of topics were always sort of top of mind for me, for sure.”

Bringing Mann in to play the part of a woman who is turning a beggar away from her door makes for a fu turn. “There was like a little dialogue portion of that lyric, and it just felt perfect for Aimee to come in and do that.” Not that we should expect to hear a lot more duets with Mann. Reminded that the two of them previously turned up singing together on an original holiday song called “Christmastime” and a soundtrack cover of the Beatles’ “Two of Us,” he can’t remember if there are any more beyond that. “Oh, God, my brain is addled — I don’t remember. We haven’t done it too much. We kind of keep it somewhat separated, but certainly those two.” But this at least makes for a third.

Penn does take what’s happening economically in the world personally, as he well knows musicians as much as anybody have seen their whole paradigm change. It’s partly why he hasn’t made an album of original music since the aforementioned 20-year-old release… although that may change, very soon.

Penn is thinking “not only of Trump and what’s happening with basically the dismantling of the New Deal, which is what’s been on the books for these guys for decades, but also just the shift in our world to a digital world. Because to whatever extent there was a middle class in music, it has been eviscerated by what’s going on. It’s not based on record sales or any of those things, and so it’s even tougher for musicians out there, because you can’t make a thing that people would like to buy, even in small quantities. So that’s tough. It’s all based on touring now, and for somebody like me who never wanted to tour, I was left few options.”

No temptation to get back out on the road at all, if that’s where the money is? “N,. For me, I mean, I never enjoyed touring. I was like the original shoegazer. I’m like an anti-performer,” he laughs. “So if I had my druthers, I would be sitting in a room making records throughout my life, but that wasn’t in the cards anymore. So that’s why I shifted to (film) composing, because it’s like at least I can be doing what I love, which is recording music. So I wish I could make records, but…”

There’s a shift in his thinking now, though. “You know, I’m doing it now” — working toward a new album — “just because I don’t give a shit anymore” whether it brings in income or not. And to that end, “I told my agent that I didn’t want to do anything this year. I did the Pee-Wee Herman documentary which just came out; I finished that at the end of last year. And I’m taking the year to write a record because I just figure I need to do it for me… for my own therapeutic use. I feel like I don’t want to produce myself again, because it’s just too many hats to wear, but I’ll figure that out later. First, I just want to generate a bunch of songs. I’m about halfway through writing a record.”

So for those who have clamored to get fresh songs as well as scoring out of Penn… hallelujah! (Exclamation point intact, unironically.)

He says it’s never bothered him when fans would come up and ask when there would be another Michael Penn album. “Oh, no, no. I’m very happy that a few people still remember me, so that’s nice. Listen, man, I mean, if I’m out in the world and somebody recognizes me or says something to me, it’s a delight.”

The full “Sweet Relief — We Can Help” track list:

Michael Penn & Aimee Mann – Hallelujah! I’m a Bum
Laura Viers – Please Let Me Get What I Want
Peter Case – Help Me
Angela McCluskey & Paul Cantelon – I Think It’s Gonna Rain Today
Watkins Family Hour – The Object Of My Affection
Peter Holsapple – I Can Help
Richard Thompson – Humpy Back Man
Ben Harper & Peter Case – Help
Willie Watson – Always Lift Him Up
Lucinda Williams – Somebody Loan Me A Dime
Dennis Witcher – That’s How I Got to Memphis
Sixpence None The Richer – The Needle and the Damage Done
Haroula Rose – A Heart Needs A Home
Victoria Williams – Sunny Side of the Street
Chris Pierce – Paper Moon
Michael Penn – Brother Can You Spare A Dime
Jonah Tolchin – Sixteen Tons
Blake Mills – While My Heart Keeps Beating Time