When Bob Dylan agreed to license one of his best-known songs, “I Want You,” for a Chobani Super Bowl commercial, it was a major coup for the yogurt company, as it sought to compete with brands like Oikos during the big game. But the news was somewhat overshadowed by fans worrying about Dylan overload when news also broke that the Man in the Black Hat himself would appear on-camera in Chrysler’s latest cinematic Super Bowl spot, endorsing the new Chrysler 200 and licensing his song “Things Have Changed” as the soundtrack.

It’s a scenario that can be unfortunate for some marketers who turn to big-name artists to help get the word out about their latest product. But it’s become increasingly common as artists themselves need multiple brands to promote their albums, fund tours and get their music in front of audiences that even radio can’t deliver

During the last two Grammy Awards telecasts, Justin Timberlake appeared in two ads for two different brands—Bud Light Platinum and Target in 2013, each using his single “Suit & Tie,” then MasterCard and Target (again) in 2014, each depicting a scene where Timberlake was surprising his fans. At MTV’s 2012 Video Music Awards, Alicia Keys unleashed a veritable onslaught of promotion for her then-new single “Girl on Fire,” premiering the song during the show itself then appearing on-camera in two back-to-back commercials (for Reebok and Citi) that also played the tune. Even Eminem, who’s only recently started saying “yes” to commercial opportunities, starred in two Super Bowl ads in 2011 for Lipton Brisk and Chrysler.

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Working with a double-booked star can have its advantages for a brand, which by nature has to get more creative with the artist and its management team to generate experiences no other company could offer, like Timberlake showing up at a fan’s house or Eminem repping for his hometown of Detroit on behalf of Chrysler.

But it can also confuse fans and sometimes measurably dilute a brand’s business, as was the case with Timberlake’s one-year deal with Bud Light Platinum. Though the singer did several programs throughout the year with the beer brand, sales of the product slowed as Platinum’s market share dipped from 1.2% in May 2013 to 1.1% in November, according to Symphony IRI (which doesn’t track bar and restaurant sales).

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How can such conflicts of commerce be avoided in the future? More transparency from all parties, for starters. Though Chrysler and Chobani knew about each other’s Dylan spots ahead of time, the secrecy surrounding Timberlake’s surreptitious album launch in 2013 resulted in a lot of surprised sponsors on Grammy night.

Sometimes, though, a “Kumbaya” moment occurs, as Janelle Monáe was able to arrange with her sponsors Target, Sonos and Cover Girl last September for an elaborate album launch party outside New York’s Intrepid Museum. It was an almost-ironic personification of a rising tide lifting all boats.

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