How do you pull off the covers?

Ron Sexsmith has always had a cadre of well-known admirers who have tweaked, tweezed and transformed his sturdy compositions, including the likes of Rod Stewart, Emmylou Harris, k.d. lang and Tom Jones.

Singer/songwriter Ron Sexsmith has always had his compositions tweaked

Singer/songwriter Ron Sexsmith has always had his compositions tweaked

TORONTO — Ron Sexsmith has always had a cadre of well-known admirers who have tweaked, tweezed and transformed his sturdy compositions, including the likes of Rod Stewart, Emmylou Harris, k.d. lang and Tom Jones.

But in the famously self-deprecating singer/songwriter’s estimation, there’s one essential key to a tossing off a truly great cover of one of his tunes: Try not to sound anything like him.

“I thought Michael Buble’s version of my song (Whatever it Takes) was pretty interesting because it was so different — he did this Latin lover take on it,” Sexsmith said during a recent telephone interview.

“And then Feist’s version of Secret Heart, I always thought was great too, because for the most part, most people who have done that song have done it kind of like me — but her version was like Euro pop or something, it was cool.”

“When someone’s doing my song, I’m always sort of flattered — whether or not I like the version, it’s interesting to hear how people interpret it.”

Music fans tend to be less forgiving. For every brilliant reinvention of a well-loved classic, there are plenty more bad or bland — or, in select cases, even blasphemous — renderings of songs that would have been better left alone.

On Sunday, CBC will premiere Cover Me Canada, a new series that will showcase the efforts of undiscovered Canadians as they reinterpret hit songs for judges including R&B crooner Deborah Cox and New Kids on the Block singer Jordan Knight.

Aside from staying in key, one of the challenges facing those hopefuls will be: what actually makes a good cover? Is it possible to outdo an original? And when is it best to just leave a song alone?

It seems like few musicians agree on the answers to those questions. After all — to slightly misquote This is Spinal Tap — it’s a fine line between cover and karaoke.

“You can’t go too far away from the way that the songs were done (originally),” Barry Manilow told The Canadian Press in a recent interview.

“I’m an arranger, and if it was up to me, I would take these songs and flip them up in the air and turn them into something totally different, but I don’t think the audiences would like that. I think when you do, I don’t know, You are the Sunshine of My Life, you’d better stay close to what the audience remembers.”

“There’s a fine line there. You want to put yourself in them but you can’t go too far.”

Matthew Morrison had a slightly different take.

The 32-year-old actor and musician has been a part of countless covers as part of the cast of Fox’s smash hit high-school musical Glee, and he recently issued a debut solo disc composed of his interpretations of songs including Somewhere Over the Rainbow, Sting’s Let Your Soul Be Your Pilot and Elton John’s Rocket Man.

He said at least applying subtle changes to the originals was essential.

“I think you have to put your own spin on it, in a way,” he said during a recent trip to Toronto.

“When you look at Glee, some people say that some of the covers we do are better than the originals. I think they’re different than the originals, I don’t know if they’re necessarily better.

“It’s an interesting question because I’m sure there’s some kind of specific answer but it’s either like a really good cover or a really bad cover. There’s never an in-between cover.”

Indeed, the margin for error is frightfully slim.

Yet it makes sense why artists try again and again to pay homage to their heroes with new takes on old tunes. A well-chosen cover can be a great introduction for an otherwise unknown band, and it can similarly help an established artist find a new audience.

Rolling Stone recently conducted a readers’ poll of the best and worst covers of all time. On the plus side, some of the renditions listed are all-time classics: Jimi Hendrix’s iconic reworking of Bob Dylan’s All Along the Watchtower; Johnny Cash’s haunting take on Nine Inch Nails’ Hurt and the late Jeff Buckley’s ethereal version of Leonard Cohen’s Hallelujah, which soars even though the song has endured more covers than a retired C.I.A. agent.

Among the offenders on the naughty list, meanwhile? Jessica Simpson’s straight-laced take on Nancy Sinatra’s These Boots are Made for Walking, Alien Ant Farm’s jock-rock version of Michael Jackson’s classic Smooth Criminal, Madonna’s undercooked rendering of Don McLean’s American Pie and tween-pop princess Miley Cyrus’s foul interpretation of Nirvana’s disaffected-youth anthem Smells like Teen Spirit.

And fans can be downright unforgiving when classic tunes are bungled by well-meaning artists. Even the artists themselves don’t always warm to revised versions of their hits.

When Randy Bachman first heard Lenny Kravitz’s cover of the Guess Who’s iconic American Woman, he wasn’t sure what to think. Kravitz added what Bachman called a “hip-hop” beat and snipped his towering solo.

He met with Kravitz at the MuchMusic Video Awards not long after — once it was clear that the song was a hit — and asked him why he made the changes that he did.

“I said to him: ‘Why didn’t you play my guitar solo?”’ Bachman recalled during a recent interview in Toronto. “He said, ‘Well, that would have been like really copying yours. Besides, I couldn’t get the guitar tone. How did you get that sound?”’

“But in a way, he took that and made it his own. He made it more modern (and) reinvented the song. Suddenly, my daughter — who was like (13 or 14) at the time — all her friends thought I was cool and hip whereas before I was just her dad. He hip-ized the song.”

It worked out well for both Kravitz — who scored a top 50 hit — and Bachman.

“It also changed his career, because his album had been out, and not doing very well, but they took (it) back, added it in as an extra bonus track, and his album then went on to be multi-platinum,” he said, noting that Kravitz also won a Grammy for his vocal performance on the tune.

“That was a milestone song for me, and for the Guess Who, and for Lenny Kravitz.”