Train’s Pat Monahan Marks 20 Years of Drops of Jupiter with Soul Vacation

At 52, Pat Monahan recalls the crucial two-decade-old moment as if it happened only yesterday. The charismatic singer’s then-nascent San Francisco outfit Train had created a music-biz stir when its eponymous 1998 debut for Aware/Columbia—self-produced for a paltry $25,000—wound up going platinum via the Top 20 hit single “Meet Virginia.” The major label had even higher hopes for its signing’s projected 2001 sophomore set, and its key composer was feeling the pressure. In spades. Most of the follow-up was in the can at that point. “But I was struggling to write the song that Columbia Records was hoping for, and there was a very small-minded agreement in the band, which was that we only write within the band,” says Monahan, who will be helming Train’s first-ever livestream concert, Soul Vacation, via the Dreamstage Live platform, at 9 p.m. ET tonight (June 25). “And Don Ienner, who was running Columbia Records then, had called a meeting for me to come in, because he was basically gonna say, ‘You’re gonna go write with writers or I’m gonna find you a song to cover.’” He already had his SFO-to-JFK ticket in hand, and was truly dreading the uncomfortable journey.

Monahan is still both baffled and awed by how the stars seemed to eerily align for him back then, at the 11th hour. His beloved mother had recently passed then; she was 68, he was only 30. And it troubled him deeply that she hadn’t witnessed any of the multi-platinum, Grammy-winning success that lay right around the corner for Train. “I never got a chance to buy my mom a house, or a car, or to do anything to say thank you, so that was tough,” he sighs today. But—as often occurs when parents pass unexpectedly—she visited her son in a dream, just in time to inspire what would become the second album’s centerpiece and title track, “Drops of Jupiter (Tell Me).” “A couple of days before that trip to New York, I went to bed, woke up, and after 15 minutes wrote all the melodies and lyrics (to “Drops”) and went and demoed it the next day,” he says. “So when I did go to that meeting, I had that song in my pocket, but I didn’t think much of it, I didn’t think it was anything at all, actually.” But when Ienner heard it, he rejoiced. “He went, ‘Whoa! This the song of the year!’ So we went from not having a song that he believed in to having the song that he believed in most,” he adds. “And I think (my mother) probably wrote it.”

The memorable track would go on to win two Grammys for Train, push its parent album past triple platinum status, and essentially define the band’s warm, neighborly folk-rock sound, rife with unapologetically radio-ready hooks that never put on arty airs above its everyman raising. Guided by the soulful, instantly identifiable stylings of Monahan, future hits like “Hey Soul Sister”—which was just RIAA-certified Diamond, for surpassing 10 million sales or streaming equivalents, one of only 47 singles to do so—were the kind of timeless, feel-good songs you might hear while shopping at Target, that immediately set your toes to tapping, an honor very few relatively disposable contemporary groups could claim after 20 years. In the beginning, a San Francisco publication sneeringly derided Train as Abercrombie & Fitch music, cutting Monahan to the quick. “But as time goes on, and we’re in Bed, Bath & Beyond, I’m like, ‘Okay. Yeah! I can back that,’” he chuckles, in 20/20 retrospect. “We’ve always had fans that were like … like us, I guess. Like me, you know? And I don’t mind. So there’s nothing you could say that could hurt me anymore—it’s been too long.”

So the Soul Vacation concert will be celebrating not only the Diamond distinction, but also the 20th anniversary of the breakthrough Drops of Jupiter, which was just reissued in both vinyl and expanded-CD editions. Train’s Bay Area-based winery, Save Me, San Francisco, is marking its own 10th anniversary—and 10 million bottles sold—with a limited-edition Cabernet Sauvignon, with part of the proceeds going, as usual, to the City’s Family House charity for hard-pressed families of cancer patients. “And the new reserve is just a really beautiful juice,” says Monahan, who regularly travels back to S.F. from his adopted home in Seattle to taste-test the grapes from his Monterey vineyards.