Guest Review: Jeremy reviews Monday Night Trivia at Redmond's Ale House

Guest Review: Jeremy reviews Monday Night Trivia at Redmond's Ale House

Here’s another guest review from one of our favorite hosts, Jeremy. If you haven’t been to one of his trivia nights, check him out at Michael Diversey’s, Rebel, and Club 162! Do you have a favorite trivia night? Email us your guest review at!


After Sidebar, I hightailed it and took the redline up to Belmont then headed up to Redmond’s on Sheffield where they do Monday Night trivia starting at 9PM. Seems like a late start, especially for a Monday, but it allowed me to hit two trivia locations in one night so I didn’t mind. So trivia started about 9:15 or so and was hosted by 3 different people, though there was one main host, though I didn’t get his name. Trivia at Redmond’s has a different theme every week and this week’s theme was Chicago trivia. Trivia consists of 5 rounds with lots of bonus questions where you can win free shots in between rounds. The first 4 rounds are 10 questions each and the last round is a lightning round with 15 questions. At the end of the night the top 3 teams gets prizes with 1st place winning $100 cash and a $50 gift certificate good on the next visit. 2nd place got a $50 gift certificate good on next visit and 3rd place a round of shots.

So the format at Redmond’s seemed okay but the execution was anything but. The host seemed like he had personality, but as he doesn’t ask a single question it’s really hard to tell. Yeah that right he doesn’t ask a single question. He is accompanied by a DJ who plays music all throughout the night and the manager also seemed to get on the microphone a tad too much. Anyway the trivia was all Chicago themed and the first round consisted of multiple choice questions about the city. The second round was all about famous people from Chicago but was way too easy as all they did was take the first few lines from each person’s Wikipedia page and you had to guess who they were. Gee who is famous for playing Han Solo and Indiana Jones??? Really that’s a trivia question??? Round 3 was all about movies based in Chicago, though the first one was about Batman Begins and the Dark Knight which while filmed in Chicago were based in Gotham City. Also in that round they had a match the famous Chicagoland actor to the suburb they are from, but they had Harrison Ford in this one again and Park Ridge wasn’t a choice. Ford was born in Chicago, but grew up in Park Ridge (I knew this because I attended the same high school as Ford). Anyway the trivia questions were neither fun nor challenging either you knew them right away or had no clue. There were no questions to really think through.

Oh I have neglected to mention that all of the questions are up on the TV screens which is a nice touch, but that’s it the host doesn’t ask or repeat questions and once they move on to the next slide that’s it. Round 4 was an audio round of songs by Chicago based artists, but they did a poor job of announcing when it would start and they played the medley only one time and you and to name the song and artist. It seemed like the majority of teams were lost on this round. Round 5 was a lightning round and they showed 15 pictures of Chicago landmarks, each picture was on the screen for 12 seconds and as soon as the last picture went off waitresses collected your answers. In between rounds there were bonus questions where all teams answering correctly won shots. The consisted of questions like name all the stops on the CTA Red Line in order or what do the 4 stars on Chicago’s flag represent. One of them was a movie quotes round were the host, the DJ, and the manager reenacted scenes from films set in Chicago.

It was actually a really clever idea and would have been fun if it didn’t stretch on too long. It was kind of like an SNL skit that starts out with lots of promise but halfway through you are going OK end this now. As far as scoring it was never really explained, but I assumed each correct answer netted you a point, though they do not announce the scores until the end of trivia so you have no idea where you stand. This is a pet peeve of mine; I mean what is the harm in announcing at the very list the top 2-5 teams after each round or the top scoring team for the round? Another annoying thing was the answers just went up on the screens as well with no announcements, so in one round they were on answer #3 before we realized and oh well. It was midnight by the time trivia was over and on a Monday night I doubt there are many people willing to stay out so late for what amounted to a pretty mediocre and poorly run night.

The bar does run a number of specials and each round it seems as if a different shot was offered 2:1. It was $3 U-Call-it and apps are ½ off as well. The waitress was super friendly, the questions were bad, the host was well hard to say as for a host he did very little to distinguish himself, the night dragged on and the food is nothing special, typical bar food. Overall I would rate Redmond’s a 1 ½ paw night if you are in the area and jonesing for a trivia night, check it out, otherwise do yourself a favor and go see Caleb at Sidebar or come to one of the many trivia nights in the city run by other groups Brain Sportz (Yeah shameless plug) Whadda Ya Know Trivia (They are really good), or Chicago Trivia Guys. I can pretty much assure you I will not be heading back to Redmond’s anytime soon.

Redmond’s Ale House
3358 N. Sheffield, Chicago
9pm to 11:30pm
Free admission
1.5 paws (out of 4)

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