Letters To Cleo started out as a Boston-based band in 1990, released three albums and then broke up 10 years later. I reviewed their album, “GO!,” which came out in 1997 and was mastered by Bob Ludwig at Gateway Mastering in Portland, when the quintet was heading up to Portland for a show to promote said release. I had really enjoyed the muscular pop/rock style of music that was created by lead singer Kay Hanley, the twin guitars of Greg McKenna and Michael Eisenstein, bassist Scott Riebling and drummer Tom Polce, not to mention the fact that the four gentlemen were also contributing vocals, as well. So when I received an email announcing that the group was actually heading back to Maine for a show, I requested an interview with a member — Eisenstein was chosen to chat with me. I called him at his home in Los Angeles and conducted a great conversation which, as it ended and I noticed that I hadn’t pressed the record button on my cassette player, was never captured, but the guitarist was more than happy to start all over again, with me apologizing profusely for my senior moment … this column starts after the discovery was made.

Q: You were talking about getting back together again after a considerable time apart?
Eisenstein: Well, we had kind of broken up in 2000, we had been petering out for a couple of years prior to that with band members doing all kinds of different projects. But in 2008 Stacy Jones, our drummer at that time, and Kay Hanley, our singer, were both in a very young Miley Cyrus’ back-up band, a teenage Miley Cyrus (chuckle). When they had a show in Boston and had a day off, we did a very impromptu, play-two-songs-up-on-stage-unrehearsed reunion and it was really fun. The crowd was very excited and it just felt great so we said, “Let’s do some shows,” and we did a little (run) and that was it for almost a decade. Then in 2016 we just kind of ran into each other at a club here in L.A., Stacy was like, “Hey, what if we did some Cleo stuff?” and I was like, “I’m into it if Kay’s into it.” She was interested so the three of us got together here in L.A. and wrote a couple of songs, and just almost immediately just started recording them.

Q: What happened next?
Eisenstein: We sent tapes back and forth to the East Coast to our other guitar player, Greg McKenna, and then he flew out and we kind of finished this little record, an EP called “Back to Nebraska,” and did some shows. At the end of that run of shows in what was November of 2016, our manager said, “Same time next year?” and we kind of made it this November thing every year since — short of 2020 when the pandemic took out those shows. So that’s our little routine now, we get back together and play some shows, our fans usually know it’s coming so they can plan because we don’t go everywhere. We only do about five to seven shows.

Q: And you mentioned that Letters To Cleo hadn’t been up to Maine in a while, right?
Eisenstein: Yeah, the last time we were up in Maine was actually for that record you mentioned receiving as a promo, “GO!” I can’t remember what the venue was, but we played there and a few of our records was mastered there by Bob Ludwig at Gateway Mastering. I remember hanging out with him on the bus after the show. He’s just the best. That was the last time we were in Portland as a band, and then I was there one more time as a sideman in 2003 when I was playing with Our Lady Peace. I have not been back to Maine since and I’m very much looking forward to it!

Q: I think what happened was that I reviewed your last album as a promotion for that show instead of an interview. That’s probably why I have that marked CD.
Eisenstein: Yeah, that makes sense.

Q: Now, should I leave out the part about Kay having COVID? I can if you’d rather I did.
Eisenstein: I don’t think that’s going to be a problem. It may or may not be why I’m talking to you and not her, I’m not sure (laughter).

Q: Where did you say you hailed from?
Eisenstein: Wayne, New Jersey.

Q: When did you move out to L.A.?
Eisenstein: In 2003, I’m almost like even right now as one-third of my life is New Jersey, one-third is Boston and one-third is L.A.

Q: I just remembered that we had also talked about what people can expect from the show at the Portland House of Music and Events in mid-November.
Eisenstein: And I mentioned that since we started doing these reunion shows we usually have some kind of angle to make the show a little different. We’ve been a pretty consistent-sounding band over our career: two guitars, bass, vocals, high-energy, melodic — we fall into the alternative/power-pop tradition. That’s the way it is in our live shows.

Q: You mentioned an ‘angle’ to these reunion shows, could you talk a little more about that?
Eisenstein: Well, in 2019 we had a Christmas EP that we performed in its entirety at the shows that year. This year we don’t have anything like a new EP, even though we have some new songs, so our angle to make this year different is we’re going to do some new arrangements and some of the songs we don’t play as much at every show. We’ll put together a little 20- to 30-minute mini set in the middle that’s going to be the songs presented in a different light than you know them from the records, but it will be bookended by our normal onslaught (chuckle).

Q: Is there anything, Michael that you’d like me to pass on to the folks reading this article?
Eisenstein: Just that, hopefully, it won’t be another 25 years between visits to Portland, but you never know, so come to the show!

Q: (Laughter) Now that’s the best pitch I’ve heard in a long, long time! And I want to thank you, Michael, for being willing to reiterate for this column.
Eisenstein:(Chuckle) I always benefit from a rehearsal, so like maybe the second round might have been better.

Q: Well, I appreciate the second effort, for sure. Is there anything we haven’t discussed that you think we should? It’s your forum, after all.
Eisenstein: Umm, no, just that we’re psyched to come and we’re looking forward to a great show and a great meal. Then it’s off to Boston for the last two shows of the tour!

Lucky Clark, a 2018 “Keeping the Blues Alive” Award winner, has spent more than 50 years writing about good music and the people who make it. He can be reached at luckyc@myfairpoint.net if you have any questions, comments or suggestions.

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