Would You Rather Tailgate With...Jim McMahon or Jay Cutler?

Last Updated on 04/14/2021 by Inside Tailgating

SportsBoy and the Inside Tailgating Crew are back with another odd look into the lifestyle of Tailgating. Last time we paired up a couple of Divas and tried to figure out which one would be more fun to have at the Tailgate. This time we want to know which group of Cheerleaders would be a better hang at the Tailgate, USC’s “Sweater Girls” or the girls from the University of Alabama? Wait a minute…who are we kidding here? If anyone was able to get these girls to their Tailgate that person would automatically move into the Pantheon of the Tailgating world. So, whom else can we choose?

Got it! This competition will be an homage to one of America’s best Tailgating cities…Chicago. The question is which Bears Quaterback would you rather tailgate with…New School QB Jay Cutler, or Old School QB Jim McMahon? As always, the criteria will flow as follows:

Appearance – who is going to wear what and how good are they going to look
Contribution – what would they make or bring or contribute
Enjoyability – is that a word? Ok…bottom line, who would you have the most fun with and why

Appearance…really? O.K. we will start with appearance anyway. This one truly depends on what kind of Tailgate you’ve got going. If you and your friends are Tailgating and wanting to look good in your new $400 pair of designer jeans then Cutler is your guy. Plus, most likely he will bring along his wife/girlfriend/fiance’ Kristin Cavallari. Even though she is about to give birth to Cutler’s spawn she will make anyone’s Tailgate a touch better to view. McMahon is going to struggle with the Appearance segment. He is probably going to show up in his busted up truck, barefoot from the golf course. As cool as that sounds, Jim is going to bring a touch of that “I went to BYU and still drank beer” white-trash element. Might be cool with all the fellas but it may scare off a good number of the ladies and that is never good. (Cutler 3.5 – McMahon 2.5)

Let us take the next step down the Tailgate grading ladder.

Contribution…this one is a tough one. If you want your Tailgate to take the next step and move into a huge space next to the Stadium then Cutler is definitely your guy. Jay is one of the new breed of Quarterbacks in the NFL that makes serious BANK. Jay could make one phone call for you and you now have the best Tailgating spot in Chicago. Cutler can also make another call and have your Tailgate catered to the Nth degree. Sometimes it’s just fun to show up and be pampered…right? Yea, I’m not sure about that one either. Tailgating is about the coming together of good friends…old and new. Jim McMahon is going to show up with a couple cases of domestic beer of your choice. He is going to grab the reigns of the grill and commence to partying. Jim may not have the pull anymore to put your Tailgate next to the Stadium, but Jim brings his attitude. The “I don’t give a f%#%” attitude. Sometimes that can be enough, but not today (Cutler 3.2 – McMahon 2.8)

Now we have come to the section that SportsBoy loves the most…Enjoyability. This is also the section where Jim McMahon makes his biggest move into the hearts of our Tailgate. Cutler may have gone to school in the SEC and know a bit about hanging out with hot chicks, but he cannot be in any way as wild to hang out with as Jim McMahon. We all know who Jay Cutler is…that asshole who believes he is better than everyone. Hey, you need that guy on your team and may even need that guy in your office, but you never need that guy at your Tailgate. You know who you do need? You need that beer drinking, play golf barefooted, dip spitting, no teeth having crazy person that everyone has fun around. Well boys and girls, that man is Jim McMahon. At the very least Jim is going to make you look like the sane person at your Tailgate. No one needs the guy who is “too good to be there” and who will probably try and sleep with your date. We all need the guy that will keep us drunk and laughing. We need that guy who will make that one day an escape to a better place. A place where no rules apply and we can spread our wings and have some unadulterated fun. That guy is Jim McMahon. (Cutler 1.0 – McMahon 4.0)

So with a huge comeback Jim McMahon makes the list as someone SportsBoy and the Inside Tailgating Crew would want to have at their Tailgate. What say you? The Tailgating public is always the deciding factor. What did we miss? Can you prove that Jay Cutler is not an A-Hole? Can you prove that McMahon is actually insane and may be a danger to us all? If you can…prove SportsBoy wrong…I dare you!