I don’t know what it is with my brain, legal marketing, and pop culture, but while watching the Grammys last night I couldn’t help but find lessons and similarities between the Grammys, lawyers and legal marketing.

What I saw last night was a living, breathing lesson on how to successfully (and not so successfully) evolve an older brand — in this case Madonna, Paul McCartney, and Annie Lennox.

Let’s do it.

#GrammyDon’t

Oh, Madonna. I love you. I prounced around my living room in the ’80s singing along as I shreaded my clothes and wore too many belts at once. But I grew up, and it’s time you did as well. But last night. Wow. Your original fan-base was just embarassed by your get-up, and your attempts to dance like you were still 24. Time to grow up … we sure have.

#LMAMKT Lesson: I am watching the AmLaw 100-200 start to shift their leadership from the older boomers (and the generation before them), to a younger one. These 50, 75, 100+ year-old brands need to carefully evolve themselves. You need to follow your client base’s lead. Some brands alienate their current client base to appease a new and hipper “it” crowd (Brobeck); while others have gracefully evolved without stunts (Skadden) finding relevenace with each new generation.

#GrammyDon’t

When you are known as one of the greatest musicians of all time — a f***ing Beatle, for God’s sake — you don’t play back up guitar and singer to anyone. You don’t align yourself with the flavor of the day to try and find relevance.  It falls flat and the new crowd wonders who the hell you are.

#LMAMKT Lesson: You are your brand. Don’t dilute it or water it down. Why are you lowering your rates? Why are you taking on lesser-valued work? Why are you entering markets where you have no reason or business case to be there? Why are you opening offices in cool, hip areas when your brand is boring and white shoed?

Don’t become the Michael Kors of legal. Don’t become your grandpa trying to be something he isn’t. And just because it worked for Skadden, doesn’t mean it will work for you. Skadden is being true to THEIR brand, and that’s why their evolution works.

#GrammyDo

Oh, Annie. Not only did you smack Ryan Seacrest down with your shade on 50 Shades of Grey, you were the epitome of style and grace on the Red Carpet, and your duet with Hozier was perfection. It was your night to shine last night and you did so by remaining 100% true to who you are and your brand: An accomplished and intellegent woman, and musician.

Last night you not only introduced yourself to a younger generation — who are now excited to learn more about you, your music, and your brand — you did so without alienating your original fan base. You made this GenExer proud.

So what’s the final takeaway?

You cannot slap a cool logo on an old brand and expect a younger generation to fawn over it. The authenticity needs to be there. Annie succeeded where Madonna and Sir Paul failed as she held true to who she was at all times. Her evolution was not awkward or forced, but a progression that made sense and was welcomed by all.