Sask. Jeopardy! contestant wins $66,101 on five-day streak
Oct 14, 2026
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You look marvelous.
Ryan.
What is SNL?
It is.
Answer, who is Ryan Robertson?
After winning 66,101 U.S. dollars last week,
Ryan joins us now to talk about his journey
from the town of Outlook to the big stage in Los Angeles.
Good afternoon, Ryan.
Hello, how are you?
I'm great.
Well, how are you feeling about that run?
I'm feeling good.
I mean, obviously, as someone who loves the game of Jeopardy,
I wish I was keep playing in perpetuity, but I mean,
you have got to lose at some point, I guess.
That is true. So walk us through
the five day streak that you had. How did it start?
So, yeah, I mean, it's pretty intense, the taping days.
So there's five episodes in a day and they shoot Monday through Friday.
and my first game was uh the thursday episode
and uh yeah i actually got off to a kind of
roaring start there um and was able to kind
of secure the game before uh before final jeopardy
uh the second game um was one of the tightest ones
and most exciting games uh in history
according to the to the lady at least sitting
in the stands by my wife uh but just winning that
meant i got a nice four-day break before the next taping day uh
and then obviously came in a lot more
relaxed um that was a monday morning uh yeah came in a lot more relaxed
and kind of rattled off a
couple of um nice wins and then uh yeah it just uh it's actually kind
of physically and mentally
grueling so that third game i just yeah kind
of things where brain was getting a bit mushy and
then uh it's kind of was an uphill battle
but uh yeah it was obviously a couple of the most uh fun
and exciting days of my life. That's for sure.
So you have four kids at home and you applied
for Jeopardy. So tell us, how did you actually get on the show?
Yeah, it was actually kind of
a long haul. So I've been trying to get on for about 15 years.
And so it starts with a quick
online sort of test. They call it the Jeopardy Anytime Test.
Yeah, you can just go on online
and take that anytime, but it's super, super rapid fire.
So it only takes like 10 minutes
or something it's 50 questions
and um assuming you meet whatever threshold minimum threshold
they have there you get invited to another audition uh
which used to be in person and
because i've been trying for a while uh i had
um i had had two in-person auditions and kind of
they went on to an online format
and yeah this latest fourth one was probably actually summer
of 2024 and i thought i was kind of out of the window of uh eligibility
but i got the call at
the end of june um saying hey you want to come down
to la um what's your availability like for
the end of august and i said i'll make myself available
so how did you prepare for all of these
tough trivia questions um well it's kind of been like
a lifelong process where uh even when i was
a kid uh my parents were reminding me of this i used
to have this like book of knowledge i'd call
it and any kind of interesting thing i'd learn i would kind
of make note of it and uh go and review
um just to kind of lock it in my memory
and then uh yeah that over time became digitized at some
point and because i am a software developer i did uh develop
an app that kind of now if i'm
on wikipedia or something and i see something
super interesting i'll just bookmark it and it
kind of gets added in there uh even using ai now
so and it will create these questions and kind of
review me um at uh later on down the line just
to kind of lock it into my memory so it's uh yeah
Just nerdy stuff like that, I guess.

