From a full-on Freaky Friday moment (where a song he wrote came belting out of Lindsay Lohan’s mouth) to crossing paths with a baby Taylor Swift and zapping us straight back to her debut era, chances are Robert Ellis Orrall has secretly been the mastermind behind one of your all-time favorite bops. And now? He’s bringing it gloriously full circle: dusting off ‘Ultimate’ — yes, that unapologetically feel-good anthem now getting a cheeky karaoke cover by girl band The Beachers in Freakier Friday’s credits — and finally dropping his own version into the world. Cue the goosebumps.
We caught up with Robert to talk about his pop culture fingerprints, the band he’s kept rocking for 40 years, and so much more.
Collaborating With Taylor Swift
You’re synonymous with Taylor Swift’s early days, having produced and co-written several tracks from her debut album. Choosing between ‘Invisible’ and ‘I’m Only Me When I’m With You’ is like picking a favorite child — so we’ll hand the hard part over to you: is there a lyric or moment from those sessions that really blew you away, especially knowing it came from someone so young? And looking back now, do you ever wonder what she might’ve taken away from those early collaborations — creatively, professionally, or personally?
On the debut, I’d have to say ‘A Place In This World.’ It was the second song we wrote (my friend Angelo Petraglia, Taylor, and I), and the idea was hers — just a girl trying to find her place in this world. It’s exactly where Taylor was in her life at the moment, and the lyrics feel effortless, real, and conversational: “I don’t know what I want / So don’t ask me / Cause I’m still trying to figure it out.” Taylor sang it on the last night of The Eras Tour, which tells me it means something to her, too.
Was there a song that didn’t make the debut album that still sticks with you? Maybe something that got shelved too soon or just didn’t fit the rollout, but you’ve never quite forgotten it?
Yes. Taylor and I wrote a Romeo + Juliet-based song that ended in tragedy called ‘Dark Blue Tennessee.’ It’s stunning, and her vocal on our work tape – to which I later added a string section – is beyond beautiful and sad. I hope it will see the light of the world someday.
You weren’t just one of Taylor’s first songwriting collaborators — you also helped showcase her at the legendary Bluebird Café, where she met Scott Borchetta. Can you take us back to that night? What do you remember, and did you have any sense of how pivotal that moment would be?
After leaving RCA Records, the traditional thing to do would have been a big splashy industry showcase, but I played the Bluebird a few times a year and suggested Taylor jump on my next round. I was so sure it would be “pivotal” that I invited my parents down from Boston so they could see someone get a record deal. And they did! I also taped it on cassette or DAT; I don’t remember which. I also can’t find the tape. Aaargh.
You co-wrote ‘Crazier’ with Taylor — a song that ended up in Hannah Montana: The Movie, sung by Taylor, and later made a huge return during The Eras Tour, with Taylor performing it live for the first time. That’s another unexpected bridge between you and the Disney universe. Did that opportunity come about because of Freaky Friday?
Yeah, that was quite thrilling when she surprised the fans in Edinburgh, Scotland with ‘Crazier.’ The place went nuts, and my phone blew up! But here’s how it happened. We wrote that song, did a demo, and it sat on a shelf until Disney called Taylor asking would she perform in the movie, and could she write a three-fourth-time waltz that everyone could fall in love to on the dance floor. She had ‘Crazier’ ready and waiting for its chance to shine. What a beautiful thing!
Freaky Friday
‘Ultimate’ was originally meant for your Monkey Bowl album — a fake band that helped launch Infinity Cat Recordings with your sons — but it ended up with Disney. Can you talk us through the decision to essentially give up something that was meant to be just yours, and how that choice ended up shaping your career, even if not in the way you expected?
Life is funny that way. First off, the song was purposely funny, “I’ve been searching for someone like you all my life / And you are the ultimate you” (yeah, duh, obviously!), and it was meant to be the title song from the first Monkey Bowl LP – until Disney called and wanted it for Freaky Friday. I had to pull it from the album because the album was coming out before the movie. It was an easy decision. But it was the title song (and cover photo) on Monkey Bowl’s second of three albums, which had a sticker on the cover that said “Includes Lindsay Lohan’s hit ‘Ultimate’ but without Lindsay Lohan.”
When you hear those songs now — whether it’s The Eras Tour revisiting ‘Crazier’ or The Beaches covering ‘Ultimate’ — how does it feel? Do you hear them the same way, or have they taken on a new meaning over time?
I’ve loved ‘Ultimate’ in all of its many variations. Lindsay Lohan nailed it. I’m a fan of The Beaches and love their version, and all the homemade versions sprinkled around the internet. In fact, the video for our version is made up of people around the world singing it with their band, their best friends, their families – plus my bandmates Kook, Don, David, and I. ‘Crazier’ has a whole new vibe when it is rocked out with big drums, guitars, and an orchestra. So much fun.
How meaningful is it to reinsert your own voice into these tracks after all these years?
I’m just having fun. I love singing songs I wrote for famous people! And it gives our show added value when we can play songs I wrote with and for others over the years, and I can tell the stories of how they came to be. And it’s really cool to be able to play them our way.
Personal Projects
You’ve got a new album coming out next month called Wrong Thing. What’s been the right thing in the songwriting process this time around? What themes or ideas have kept your pen moving?
Wrong Thing is our first all-new studio album since The War Between Us, which we recorded in 1986 but finally released last year. There’s my favorite theme – unrequited love – and some pretty heavy sh*t, including a couple of the saddest songs I ever wrote. Some songs were started in the past, and some just spilled out of me in a single morning. It’s a pure pop record that includes some great collaboration between the four of us, including ‘Where The Gone People Go,’ a song we wrote together on my porch as the rest of the album was being mixed by Steve Marcantonio. The very same Steve Marcantonio who assisted with the mix of our first album, Fixation, in 1980.
You’ve been with your band for 40 years — which is an insanely long time by any standard. What’s kept that bond so strong after all these years? What’s the secret sauce?
Well, we’re four brothers, four geezers that spent five years in a red van together in the ‘80s. We love each other and have a ball making and performing music together. Even back in the wild ‘80s, we never had blowouts or fights. Now we’ve got all the old stories and a million laughs along the way. It’s a reunion for life.
You’ve got two gigs coming up: The Cut in Gloucester later this month and then the Two to Lou Music Festival in September. How do you keep performing with your band feeling fresh even now? Does every show still carry some of that ‘first time’ magic?
We reunited for one sold-out theater show in ‘23, and it was super emotional. It was just “Wow, we gotta do this ‘til they put us in the ground.” So two shows in ‘24, four two-hour-plus shows in ‘25, and four albums in the meantime. So far, every show has been more exciting than the last. We plan to keep on keeping on and keep laughing our way to the end.
Are you heading to one of Robert’s upcoming gigs? We know you want to—honestly, we might just have to pull a cheeky Freaky Friday body swap so we can be the ones rocking out in your place. 🎸 Check his website for all the deets, then flood our Twitter, Instagram, and Facebook with every glorious video. We’ll be living vicariously through you. Promise.
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