Pat Monahan & Pete Wentz - 'I told Pat I liked his wine. He sent me a crate of 50 bottles'

Pete Wentz, 35

A prolific member of Chicago's punk scene in the late 1990s, Wentz (right in picture) formed acclaimed rock group Fall Out Boy with lead singer Patrick Stump in the early Noughties. Their five albums clocked up significant sales, with the track 'This Ain't a Scene, It's an Arms Race' reaching number two in the UK. Wentz lives in Los Angeles with his partner and two children

When I took some time off from Fall Out Boy, in 2009, I reached out to Train about writing and directing one of their videos ["If It's Love", on their 2009 comeback album, Save Me, San Francisco]. We met on the video set. Pat was the "Drops of Jupiter" and "Hey, Soul Sister" guy – some of the biggest songs – so you never know if someone like that is going to be cool or just… very interesting.

I realised we were kindred spirits pretty quickly. I had an idea for the video about imagining what Train had been up to during their hiatus, with this joke about him at home with a TV dinner, but Pat wanted it to be even darker. I like anyone who's able to make fun of themselves, as I don't think everyone in this industry has that capacity.

To me, being with Pat is like being seeing my future a bit – like looking at tarot cards. He's gone through difficult times in his life and with his band [which similarly went on hiatus, in 2006] and it showed me that maybe there was light at the end of the tunnel. Since he had gotten back together with Train they were bigger, better and healthier and, 10 years after [the band first formed] no one expected that success to happen again.

When you're in a rock band, it can be hard to figure out how to connect with your family. But when he was sitting on the set, he had his baby daughter in his lap, looking at him. He didn't know I was watching but I was thinking, there's a great guy – he may be just coming off of "Hey, Soul Sister" but he's being a dad. And I'll always remember how it made me realise that maybe you can have it all.

I've been to his house and talked and hung out with him. You don't see his humour in the Train songs, but that devilish side is an important facet that makes him more likeable. I remember once how Pat and his daughter threw loo roll around the trees of some neighbours as a prank; I had a new respect when I saw that secret, funny side of him.

I like people who think in a grand way, and sometimes he has these out-there ideas about Train memorabilia. A few years ago I tried these Train wines [Monahan runs a vineyard] and I told him I really liked them. A few days later Pat sent me a crate of 50 bottles ; my housekeeper thought I was a raging alcoholic.

Pat's said he'd rather be remembered for being a good guy than for his music. But Henry Ford was a Nazi sympathiser, and he's mostly remembered for what he created. I know that my family realise that I'm a decent guy, as do my friends, but I think in terms of legacy now – and to me, the songs are my legacy; I want my songs to live beyond me.

Pat Monahan, 45

Monahan is the lead singer of rock band Train, whose break-out song, 2002's 'Drops of Jupiter', won the Best Rock Song Grammy. The band has since sold more than 10 million albums. Monahan lives near Seattle with his wife and two children

We met five years ago when Pete directed the music video for our single "If It's Love". We are both managed by Crush Management and as Pete was on hiatus from Fall Out Boy, he had the idea to direct one of our videos. He got in touch and asked if we would consider it.

He knows that we notoriously dislike red carpets so he said, "Wouldn't it be cool if we do glamorous scenes of you on a red carpet?" It was a fun shoot and it worked great, and Pete and I became friends.

When you're in a band, getting away from it sounds like a great idea. But when it actually happens, it can be pretty scary. Pete was going through it then, and I'd been through that, too, and it connected us. I'd made a solo record [Last of Seven, in 2007] and if that had produced more income, I wouldn't have been in Train any more – though I'm glad it worked out the way it did.

Pete is like Peter Pan to me, full of lovely youthful enthusiasm that I just want be around, as it reminds me of what I would like to have more of. He doesn't sit still very long; he's always in this constant state of oscillation, which I find really funny.

I was happy for him when he broke up with his wife [the singer Ashlee Simpson]. I split up with the woman I was not supposed to be with, too, and though I could see him entering into that scary, difficult period, I told him that the other end of it is beautiful and magical.

With Fall Out Boy, he broke a stereotype: there's not many bass players who can take over a band like he has; he's a great lyric writer but he also understands pop culture, and he gets it like nobody else.

I have four kids and he's got two, so that's another reason we get along; once you have a child you aren't allowed to be a child any more and that shift is a great equaliser. In this industry we are all pretty selfish men, but when you have kids you think, "Oh boy, I've got to start figuring this stuff out."

Pete is far more famous than I have ever been, and I expect famous people to be odd. There's a saying that, if you are like us, you get the joke, that you can't take the music industry seriously. When you walk off that stage, you become a person again, and not that icon any more. You can never be who your fans think you to be, and if you don't understand that, you're like those [rock stars] from the 1980s who were too difficult to be around. Pete gets the joke.

Train's latest album, 'Bulletproof Picasso', is out on 15 September (savemesanfrancisco.com)