![Jack Black was so cool in 1993's Demolition Man it's taken me roughly 20 years worth of watches to spot him! : r/OldSchoolCool Jack Black was so cool in 1993's Demolition Man it's taken me roughly 20 years worth of watches to spot him! : r/OldSchoolCool](https://i.redd.it/zlneayhag5h41.jpg)
Jack Black was so cool in 1993's Demolition Man it's taken me roughly 20 years worth of watches to spot him! : r/OldSchoolCool
![Naff | Be Everyone's Problem on Twitter: "I like podcasts bc I get to learn about movies Jack Black was in LIKE DEMOLITION MAN?? https://t.co/3HGhcQxesa" / Twitter Naff | Be Everyone's Problem on Twitter: "I like podcasts bc I get to learn about movies Jack Black was in LIKE DEMOLITION MAN?? https://t.co/3HGhcQxesa" / Twitter](https://pbs.twimg.com/media/Dz91W7LUUAAwpqt.png)
Naff | Be Everyone's Problem on Twitter: "I like podcasts bc I get to learn about movies Jack Black was in LIKE DEMOLITION MAN?? https://t.co/3HGhcQxesa" / Twitter
![In both Demolition Man (1993) and Ice Age (2002) Jack Black plays Denis Leary's henchman : r/shittymoviedetails In both Demolition Man (1993) and Ice Age (2002) Jack Black plays Denis Leary's henchman : r/shittymoviedetails](https://preview.redd.it/in-both-demolition-man-1993-and-ice-age-2002-jack-black-v0-w64t56zlxf091.png?width=640&crop=smart&auto=webp&s=69723f13f3c83fc718a15fbe403d8378578cc1d8)
In both Demolition Man (1993) and Ice Age (2002) Jack Black plays Denis Leary's henchman : r/shittymoviedetails
![Timothy Johnson on Twitter: "@kateleth Jack Black in Demolition Man https://t.co/zpoEi0gDlg" / Twitter Timothy Johnson on Twitter: "@kateleth Jack Black in Demolition Man https://t.co/zpoEi0gDlg" / Twitter](https://pbs.twimg.com/media/EB4B6iYWwAEHnOs.jpg)