Alright, so I got into this thing today, watching Frank Caliendo do his Jon Gruden impression. Man, that guy is something else! I’ve always been a fan of impressions, and Caliendo is one of the best, no doubt.
First, I pulled up some of his videos online. I gotta say, it’s not just the voice, but the whole package. The way he squints his eyes, the hand gestures, and that signature head tilt – he’s got Gruden down to a T. I started by just watching, trying to pick up on the little things, you know? The nuances that really make the impression pop.
Then, I figured I’d give it a shot myself. I mean, how hard could it be, right? Famous last words. I started with the voice, trying to get that gravelly tone that Gruden has. I practiced saying some of his classic lines, like “This guy right here” and “I’ll tell you what, man.” It sounded more like a sick cat than Jon Gruden, but hey, gotta start somewhere.
- Focus on the voice: I spent a good chunk of time just working on the voice. I listened to clips of Gruden talking, then tried to mimic him. Repeated it over and over, recording myself to see where I was off. It’s tougher than it looks, that’s for sure.
- The mannerisms: Next, I tried to incorporate some of the physical stuff. The squint, the head tilt, the way he kinda juts his jaw out. I stood in front of the mirror, feeling pretty ridiculous, but hey, gotta commit, right?
- Putting it all together: This was the hardest part. Trying to do the voice and the mannerisms at the same time was like trying to pat my head and rub my belly while juggling chainsaws. My brain just couldn’t handle it at first.
After a while, I started to get the hang of it, kinda. I wouldn’t say I was ready for Vegas, but I could do a decent Gruden impression for a few seconds before I cracked up.
I called up my buddy, who’s also a big football fan, and tried it out on him. He laughed his ass off, which was a good sign, I guess. He said I sounded more like Gruden’s long-lost cousin from the backwoods, but it was still funny.
The Results
So, yeah, that was my day. Trying to master the art of the Jon Gruden impression, courtesy of Frank Caliendo. It was a lot harder than I thought, but also a lot of fun. I’ve got a newfound respect for impressionists, that’s for damn sure. It takes some serious skill to pull that stuff off.

I realized that it takes a lot of observation and practice. I had to watch and listen to both Caliendo and Gruden very carefully. I had to try out different things and figure out what worked. I had to be patient and not give up. I had to be okay with sounding silly at first. All in all, it’s a fun process, and I enjoyed this day.
Maybe I’ll keep practicing and see if I can get better. Who knows, maybe one day I’ll be able to do a full-blown Gruden monologue. Until then, I’ll just keep chuckling at Caliendo’s videos and saying, “This guy right here, he’s a special talent, man.”
Anyway, that’s my story. Hope you got a kick out of it. If you’re into impressions, definitely check out Frank Caliendo. And if you’re feeling brave, maybe give the Gruden impression a try yourself. Just be prepared to sound like a dying walrus at first.