I've been to Jacobs many times and it never ceases to amaze me. You'll always get a wonderfully cooked steak with great service.
I must give a shout-out to our server, Samuel. He gave a great introduction and walkthrough of the menu to my colleagues who were first timers. He also helped make a side dish into a halal friendly option for my colleague.
As for the menu, you can skip the apps. They're nothing special and imho, they're overpriced and underwhelming. You go to Jacobs for the steak.
I've eaten many different cuts but I was impressed to see them offering more interesting international cuts. My colleague and I decided to split two steaks, a traditional option and then a more artisanal option.
I had a 24 oz bone-in ribeye from Arkansas which was absolutely amazing. The marbling was fabulous. It just melted in your mouth. They rendered the fat cap beautifully so it didn't have chewy bits of fat. It was aged for 55 days iirc. It had such a beautiful aroma. This was the traditional steak.
The second steak was the highest grade of steak out of Scotland. The producer stamps the cow for authenticity purposes. I can't remember the name of the brand. We had the bone-in strip. It's not aged as long (30 days) since it's grass fed. So it has a bit more of a chew and it's less sweet. We liked it but the traditional steak was much better. For transparency purposes, I'm a ribeye guy. But I still think the meat itself didn't taste as good or have the same buttery texture as the traditionally raised ribeye from Kansas.
We had the potato puree, tossed mushrooms with a olive oil and garlic sauce which Samuel hooked up since the original recipe included marsala wine. My colleague is Muslim and Samuel took care of it. We also had the duck fat fries. The sides were all delicious but the fries were the best. They were crispy on the outside and fluffy in the inside.
For dessert, we ordered a 6 oz Australian 9+ marbling score fillet. It was very good but honestly, it's better to pay another $100 and get A5 from Japan. It's levels better than the Australian equivalent. There's just nothing that compares to an A5. It's the ultimate luxury in steaks and it actually lives up to the hype!
One last thing, don't go to Jacobs if you're frugal or not comfortable paying $200+ on a meal. If you want to splurge and/or celebrate, there's no better place than Jacobs for steak. It's not even close. I've covered all of the top spots in Toronto and no one touches Jacobs. It's not just the steak, their service is amazing. They aren't snobby which is so refreshing given the price point of the restaurant. I saw people in track pants and others in suits. It's such a great vibe. Ask for the main dining room upstairs to get the real experience. The piano bar is ok but if it's an occasion, make sure to get the main dining area.
We had a bottle of red wine which went very well with the steak. It was a California Cab Sauv.