27/01/2014 07:14 GMT | Updated 26/03/2014 05:59 GMT

The Delicate Dynamic of Musicians and Brands

From a commercial standpoint, musicians and brands have spent years trying to make the most of each other. Some of those partnerships, like Michael Jackson and Pepsi back in the 1980s, have become the stuff of marketing legend.

The recent deal between drinks giant Diageo and rapper Sean 'Diddy' Coombs, with each owning a 50% stake in niche tequila brand DeLéon, is yet another example. However, the truth is that alliances between music artist and brand are notoriously difficult to navigate and the success rate remains small.

Although other entertainers, be it sportsmen, TV stars or film stars, need to constantly manage their image with regard to their commercial relationships and be wary of over-exposure or the wrong kind of association, the danger is greater for both sides with successful musicians.

For the brand, there is the fear of bad-boy behaviour coming out to tarnish the brand or even the waning of the once-bright star. For the star, there's the battle with the perception of selling out, chasing the corporate dollar, not being genuine or 'real' enough.

The most genuine of all commercial partnerships between brand and talent, for me, comes when there is a very clear and obvious relationship. When Frank Sinatra was accompanied by a bottle of Jack Daniel's whiskey onstage and at dinner, any future commercial relationship made sense, regardless of the size of the transaction.

But where it is less genuine, or doesn't make sense to me, is when a performer might change his or her commercial arrangements between competitors; for example, were Beyoncé to start drinking Diet Coke once her Pepsi sponsorship ran down, or Madonna to support Absolut when her live shows are part-funded by Smirnoff.

For the purists, ideally no money would change hands; an artist would be happy to be seen using the brand's product; the brand would benefit from awareness, likeability and sales from being seen being used by the talent; and the artist would benefit from VIP treatment from the benevolent blue-chips. However, such cases are few and far between.

At the other end of the spectrum are unique deals like this one between Diddy and Diageo, where the financial agreement is clear from the off and the meaning of the relationship in no doubt. For Diddy, it looks like an excellent piece of entrepreneurialism, driving his fame and his brand and no doubt his value and wealth. And the same goes for Diageo in terms of awareness, sales, value and volume.

These days, like his rapper peers Jay-Z and Dr Dre, Diddy is as much a businessman as an artist (perhaps even more so) and is relatively 'safe' in terms of reputation. He no doubt indexes well with certain demographics that will be critical to Diageo's global ambitions, and in this case in the tequila market. His involvement will no doubt do far more for the brand than it would were he not to be so heavily visible and involved.

The truth is that music fans accept and sometimes even welcome the alliance between band/artist and brands. Most of them certainly recognise that some of the great experiences and entertainment that they enjoy may not be possible without the financial support of the business whose logo is on the ticket.

And yet, the desire for musicians to deliver such a relationship meaningfully is still fairly limited. Sure, they want the money, but they're rarely prepared to fulfil the genuine link with the brand that the investment merits.

For Diddy and Diageo, a brave and honest transaction will undoubtedly reap significant rewards for both sides and provide both with what they need. This latest alliance highlights that some musicians see themselves as businesspeople as well as talent - and are prepared to act commercially.