It’s entirely possible that you don’t know much about the band Train, or perhaps you don’t know them at all...but you certainly know their music. Whether it’s their breakout smash “Meet Virginia,” their Grammy-winning tune “Drops of Jupiter,” or perhaps their more recent successes such as “Hey Soul Sister” or “Drive By,” the music of San Francisco-based pop-rock outfit Train will find you one way or another.

The band is headed out on tour with the Goo Goo Dolls this summer, and lead singer and songwriter Pat Monahan took some time to talk to me about what they’ve been up to lately and how they were able to turn the names of their albums and songs into a side hustle.

We're six months out from the release of Train’s Greatest Hits collection. Did you ever think that you would get to a point where you were putting out a greatest hits album?

Pat Monahan: I never wanted to put a greatest hits out, because it always seems like the end of an era, whether or not that's the case. I hope not. I hope to keep making music that will somehow be relevant. It's not an easy thing. There are always new people that you're competing with, but I also believe that the music world has changed in such a positive way that if it's good enough, people will find it.

So, I don't know. I gave in to putting out a greatest hits, because these guys convinced me that it was a better way for people to find us online that might not know all of our music. But once they see “Drops of Jupiter” or “Hey Soul Sister” or “Drive By,” then they can see all the other ones and go, "Oh yeah, right, I know that one!" So, it just made more sense.

Never thought about it like that. It's a good streaming strategy.

Monahan: Yeah, that made a lot of sense to me, but all the greatest hits that I love, except for maybe James Taylor and The Eagles, it just seemed like, "Okay these guys are going away. Take care." But, I guess Aerosmith had a couple of greatest hits right?

U2 puts one out every decade.

Monahan: Yeah, right. So, we'll just do that.

We were really happy to see the two new cuts on it. One cover and one original. If you're going to do a cover, why was “Careless Whisper” the one that you went with?

Monahan: It was really just a matter of fun, because my managers manage Weezer, and they were recording Toto. My manager was like, "Young people are waking up to the ‘80s." So we talked about half a dozen songs and “Careless Whisper” seemed like one that would be fun because I love George Michael. It really depended on if Kenny G. was going to do it or not, and when Kenny said that he would, it became clear that we should record the song.

Train just turned 20...or is it 21 now maybe?

Monahan: Yeah.

What's something you would like to do that you haven't done yet with the band?

Monahan: There's a lot of things. I'd like to headline Wembley Stadium and Giants Stadium in San Francisco where the San Francisco Giants play. And, I don't know there's a lot of other things. It used to be that I wanted to headline Madison Square Garden, and we did that last year with Hall & Oates, so it's fun to keep knocking them off you know?

You just launched a new wine collection. What made you want to do that, and why name it Drops of Jupiter versus any other song title?

Monahan: Well, we made a brand years ago and called it Save Me, San Francisco. The idea started because we're a San Francisco band and wine is a massive Bay Area luxury item. We wanted to provide a really great bottle of wine for a reasonable price for Train's fans, so we made a $10 bottle of wine called Drops of Jupiter and it was a Petite Sirah, which nobody really knows much about unless you really know about wine.

Then we made six other varietals, and I think it really took away from the original concept. It was all to benefit a charity in San Francisco called Family House, which is a house where a lot of low-income families with their very sick children who have life-threatening illnesses stay while the kids get sorted out at UCSF hospital.

We sold millions of bottles of wine and helped out the charity enormously and we thought, “How can we move forward?” So we took Drops of Jupiter as a label and made three varietals at a higher price point that is a higher level wine. So, that's how it all started, and that's where we are right now, and it's doing really well.

I'm surprised even the $10 price point because I was about to say $20 is a great number. I would buy a $20 wine, let alone that it goes to charity.

Monahan: Yeah, and you know, I feel like the world of wine is a lot like the world of music where, sometimes a song sneaks through and defies the odds, and sometimes a beverage defies the odds. We've already defied the odds a couple of times, and I hope that $20 is going to be a reasonable price for people to spend on a really great product, and it'll benefit a great charity. And so, Drops of Jupiter just seemed to be the obvious song title.

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