Jay Cutler has always been an entertainer, intentionally or not. He put together a productive NFL career loaded with highlights of every sort. Chicago Bears fans have fond memories of him, especially after enduring years of Mitch Trubisky and Justin Fields. He even showcased his talents in front of the camera on reality TV alongside ex-wife Kristen Cavallari. The guy had a great sense of humor and biting wit. It is unfortunate he didn’t pursue a career in television. He had a knack for it.