Madonna performing during the 2011 Superbowl halftime show(CP)

It's a toss-up between which is more uncomfortable: having root canal surgery or watching Madonna desperately try and stay relevant.

Once one of the most respected entertainers in the business, the 54-year-old singer's feverish attempts to appear young and hip with fans are tarnishing the reputation she's spent decades earning.

The latest ploy for popularity saw Madge invite "Gangnam Style" singer Psy on stage at her Madison Square Garden concert this week only to crawl through the YouTube sensation's legs and proceed to ride him like a pony.

This embarrassing sight comes just days after the "Music" singer stripped down on stage to raise money for Hurricane Sandy victims.

The removal of any and all clothing has become the mainstay of Madonna's world tour, with the mom of three even stripping with son Rocco on stage and flashing a nipple to a Muslim audience.

Even her pom-pom infused performance of "Give Me All Your Luvin'" at the Super Bowl earlier this year with rapper Nicki Minaj, in which she attempted an awkward hand-stand move on stage, was more than a little cringe-worthy.

Not only is Madonna's unhealthy obsession with turning back the clock threatening her professional legacy, but it's already said to have cost her marriage to ex Guy Richie, and it's certainly what's fuelling her fetish for twenty-something boy-toys.

Even the adoption of daughter Mercy from Malawi three years ago was surely a subconscious effort to thumb her nose at the passage of time.

Madonna's long-standing feud with 26-year-old Lady Gaga - who she accused of ripping off "Born This Way" from her "Express Yourself" hit - also seems to be rooted in the jealousy of youth and all the potential that comes along with it.

This is a time in Madonna's career when she should be basking in her tremendous success - having sold a whopping 300 million records in her career - not hustling like she still has something to prove. She can tour the world all she likes as long as she keeps her nipples in check and stops using it as a forum to cut down young stars like Lady Gaga who she really should be mentoring.

There's no denying Madonna is one of the most iconic entertainers on the planet, but at the rate she's going, the history books may remember her in a far less flattering light, something she may want to consider the next time she strips for a cheap headline.