How Detroit's Tim Roberts Helped Catapult the Career of Pop-Country Superstar Taylor Swift

Seven years ago, two kids skateboarding in a Northville restaurant parking lot witnessed an historic moment in pop music history – and had absolutely no idea what they were watching. But more about that in a moment.

Tim Roberts, the operations manager and program director for Detroit’s country WYCD-FM (99.5), will be a marked man this weekend [May 31-June 2] at the WYCD Downtown Hoedown in Comerica Park. It’s like that for him year-round.

WYCD-FM's  Tim Roberts

You see, the Allen Park native has what people in the music industry call “a great ear:” a national broadcasting publication has proclaimed him the best country radio programmer in America two years running, and in more than 30 years in the business he has seen the launch of virtually every contemporary country act working today. He knows, and can promote, a hit when he hears one.

So band managers, agents, publicists, musicians – at an outdoor event like Hoedown, folks hunt down Roberts backstage like he’s got the only key to the porta-potty. “I get a lot of acts thrown at me, to the point where it actually gets tiring after a while,” he says. “Not in a bad way, but it’s just the time [involved]. Another new artist. ‘Listen to this,’ ‘Listen to that,’ over and over again.”

However, it is Roberts’s willingness to lend his ear to unknown performers that led to what he now calls “the famous story about Taylor Swift,” and his part in helping to propel the career of the international pop-country superstar. But let’s allow Roberts to recount the tale:

“I get a call from Jack Purcell, VP of promotion at Big Machine Records. Jack was my rep when he was at Warner Bros., I’ve known him for years. He says, ‘We’re starting this new label, and we really want you to hear our new artist.’ I’m thinking, ‘Oh, for heaven’s sake.’ I think I already had five appointments in two days before they were coming to town, plus I found out she [the artist] was 14, 15 years old. I think to myself, ‘Oh, this is going to be super weird.’

“I say, ‘Well, let’s go to dinner. Then it won’t be so awkward. We’ll have dinner, conversations, good food.’ I should have taken them to some uniquely Detroit place, but we ended up at P.F. Chang’s. I asked, ‘Does she like Chinese? Yes? Fine.’

“So we have dinner and of course, she’s as charming as could be. I could tell she was really smart. And her mother, of course, was wonderfully charming, too. My wife. Lori, was with me, and Jack, and we ate and had this great conversation. And at the end of it she goes, ‘Well, do you want to hear my songs?’

“I go, ‘Yeah, I’ve got a CD player in my truck.’

“She says, ‘No, no, I want to play you the songs.'

“‘Well, Taylor, we’re in P.F. Chang’s. That’s going to be a little weird.’

“She goes, ‘No, I’ll sit on the back of your truck and I’ll play you the songs in the parking lot.’ I thought that was strange, but I said OK.

“So we go out in the parking lot, she whips out her acoustic guitar and she played me the songs ‘Tim McGraw,’ ‘Teardrops on my Guitar’ and 'Should've Said No.' Three songs: two of them became No. 1 (hits) and 'Tim McGraw' was like no. 5. And I was like, 'Oh, my God.' I'll never forget it, because really no one was paying attention to us at all, except these two kids who were skateboarding nearby, just doing their little thing, you know. Since then I've often thought, 'If they'd only known what they were listening to!'

"She was incredible. And after it was all over the last thing she said was, 'I’d love to see 8 Mile.' She remembered the movie, and I said, 'Well, ironically, 8 Mile is only one mile this way.' So I took her over to 8 Mile and Haggerty, and she goes, 'This is it? There's a shopping center!' And I go, 'Well, it looks a little different if you go down that way about five miles.'

"Then we said goodbye, I got back in the truck with my wife and I went, 'Is it just me, or was she amazing? They all sounded like hit records!’ And my wife, who was in the radio business a long time, said, 'Yeah, they did. She was awesome.'

"I said, 'I have got to start playing that record immediately!' it was the song about Tim McGraw. I started playing it and it started getting real popular. I mean, you could just see it. And I was telling people, 'You’re going to think I’m crazy, but this Taylor Swift 'Tim McGraw' song, it’s just blowing up!'

Roberts and That Girl

"She came back to Detroit a short time after that and we had her on our morning show [Dr. Don With Rachael and Grunwald]. There's a part in the song where the chorus goes, 'When you think Tim McGraw/I hope you think my favorite song.' Well, she went back in the studio and re-cut it so it went, 'When you think Tim McGraw/You think Dr. Don and Grunwald.' They remixed the whole thing and sent it back to us. We started playing the custom version, and as soon as we put it on it exploded. The phones were already blowing up over the song, and I was playing it in heavy rotation before anybody figured out who this girl was.

"And we’ve been friends ever since."

Roberts acknowledges that now that Swift is all grown up, headlining stadium tours as a musical megastar, "I don’t talk to her as often as I did. When she was growing up, though, I used to really keep in touch with her frequently.

"To the point where after one of the award shows years ago, she had just won Best New Artist. She was brand new. And she saw me in the hallway and just ran up and jumped into my arms. Everybody's going, 'Who the hell is that guy? I went, 'Man, I’m just a radio guy.' But we hit it off.

"She knows my daughter, she knows Lori. In fact, when she was playing Ford Field [May 4], my wife couldn’t make that show. When Taylor saw us backstage, the first words out of her mouth were, 'Where’s your crazy wife?'"