5 hilarious moments in Chicago Bears history starring Walter Payton, Mike Ditka, Jim McMahon, and more

The Chicago Bears have a grand total of one Lombardi Trophy. Not great, certainly, but better than the Vikings, Bills, Bengals, Falcons, Panthers, Cardinals, Titans, Chargers, Browns, Lions, Jaguars, and Texans, who have a combined total of zero Lombardi Trophies.

The Bears have something else the Vikes et al lack: Pop culture relevance.

Chicago’s NFL franchise may not own the hardware, but it most definitely boasts a goodly number of priceless comedic moments that remain in the public consciousness, even decades later.

Here are five:

Walter Payton x Don Cornelius

Before the Bears made Walter Payton the fourth pick of the 1975 NFL Draft, the running back starred at Jackson State University, racking up 464 points and a then-NCAA-record of 3,563 yards.

Something else he did at Jackson State: Dance. And he was good. Damn good.

So good, in fact, that on September 15, 1973, we were able to watch Sweetness drop some steps on the old-school dance show, Soul Train. Admittedly, Payton’s moves were legit, thus the performance wasn’t the least bit funny. But side-by-siding Payton’s silkiness on the floor with his slickness on the turf is pretty darn amusing.

Was Payton ready to become a member of the Soul Train dance troupe? Nah. But on that magical day in ’73, the Hall of Fame legend put on his boogie shoes and disco’d his way into immortality.

Ditka’s Gonna Ditka

During a majority of the press gaggles throughout his 11-year tenure as Chicago Bears coach, it was always a question as to whether Mike Ditka was naturally funny, or whether he was he was going out of his way to put on a show, or whether he was simply a curmudgeon whose bon mots unintentionally came off as chucklesome.

Regardless, the mustachioed one cracked up reporters and fans alike, especially after losses, when he’d gleefully trash his team, the opposing team, the opposing team’s coaches, and oftentimes himself.

Ditka’s mustache/sunglasses/sweater combo platter was also hilarious in his own right, but that’s for a column about Chicago Bears fashion icons.

Live From Chicago, It’s Saturday Night!

The brainchild of sketch comedy writing legend Robert Smigel, Bill Swerski’s Superfans made nine appearances on Saturday Night Live between 1991-1997. The core group of SNL Superfans—Smigel, Chris Farley, and Mike Myers—was joined by a revolving door of guests, among them Michael Jordan, Joe Mantegna, John Goodman, and, most regularly, George Wendt.

Unfortunately, Dan Hampton—certainly one of the funniest of the ’85 Bears—never made the cut.

Headbandgate

Back in the day, it was a problem if a player wore an item of clothing on an NFL field that sported a corporate logo. That’s opposed to today, when every item of clothing on an NFL field sports a corporate logo.

Jim McMahon was an adidas guy, and as such, wanted to sport his sponsor’s signifiers as often as possible. NFL Commissioner Pete Roselle wasn’t on board, so at the NFC Championship Game on January 12, 1986, McMahon gave the Commish a middle finger of sorts, donning a headband with the word ROSELLE Sharpie’d on the front.

Roselle didn’t find it the least bit funny, and fined the punky QB $5,000.

During his next game—that game being Super Bowl XX—McMahon wore several headbands, some of which were to raise awareness of charitable causes, among them the Juvenile Diabetes Foundation.

That time around, McMahon wasn’t fined.

Super Bowl Shuffle

The story of the Bears’ absurd “rap” video has been told time and again, so let’s just go ahead and rank the vocalists from worst-to-less-worst:

10) Steve Fuller

Ugh. Just, ugh.

9) Mike Singletary

It feels like Samurai Mike listened to “Rapper’s Delight” 1,000 times and decided, “I’m going to do the exact opposite.”

8) Jim McMahon

Mac’s flow was terrible, but he gets bonus points for pulling off the “Punky QB” line.

7) Gary Fencik

The Yalie is one of those guys who does everything well. Except rap.

6) Otis Wilson

The vicious linebacker looked like he was having a whole lot of fun, which somewhat makes up for his iffy delivery.

5) Walter Payton

It’s possible that his Soul Train experience helped Payton come off as not horrible.

4) Willie Gault

The receiver was one of the most confident performers on the stage, and confidence goes a long way.

3) Mike Richardson

It’s up in the air as to whether the cornerback came to the session already nicknamed “L.A. Mike,” or whether he earned the moniker at the gig. Regardless, it’s pretty dope. (Update: Bears On SI's Gene Chamberlain tells us, "Mike Richardson was L.A. Mike before the Shuffle. [Bears defensive coordinator] Buddy [Ryan] referred to him as L.A. Mike from the day he was there: Lazy Ass Mike." Buddy's gonna Buddy.)

2) Richard Dent

Dent is one of the scariest men to ever play the game, and even though he’s currently 64-years-old, we’re too frightened to say anything bad about him. So well done, Rich!

1) William Perry

Despite the fact that the 1985 Bears were loaded with Hall of Famers, the Fridge, an above-average player at best, remains one of the team’s most beloved characters. He’s a garbage rapper, but his innate charm overcomes his lack of vocal skills.