I LOVE this question.
Beefcake is easiest, and the big contributor there is that EVERYTHING is scaled to your current ability. You have your training max, and it determines how much you lift. It never really forces your reach to exceed your grasp. The most challenging part is that 20 minute time cap, and that’s a recommendation rather than a requirement. None of this to say it’s an easy program, but of this group, this is the level 1 boss.
Mass Made Simple is next, for similar reasons. Dan John walks you through each and every workout, and everything is based on your current ability EXCEPT for the squats. Those are written in stone. If you weigh this much, you squat this much. HOWEVER, the biggest sets are “to 50”, rather than “a set of 50”. It gives you an avenue for escape, in that you can NOT get the 50 reps in one set and still be meeting what the program lays out. But if you shoot for the moon, it’s a challenge, and you can always go for extra credit and move the weights in the next weight class up. CAVEAT: BECAUSE I am so bad at cleans, my complexes may have, in fact, been artificially reduced in terms of difficulty, which DOES impact the overall program difficulty, as you do the complexes before the high rep squats. A stud like @BrandonCrawford might find that the program is especially cruel BECAUSE he’s good enough at the clean to move some challenging weights for the complexes.
5/3/1 Building the Monolith done MY way, in under an hour, is next. And I suppose I should have mentioned this with beefcake as well, but especially so with Monolith: those assistance exercises ARE the challenge. Beefcake is a little bit more forgiving with 50s, but if you are doing a legit 100 chins and 200 dips on top of everything else the program demands, it’s EXHAUSTING. I still tell the story about the first time I did day 1 in under an hour, I spent what felt like 15 minutes in the shower just staring at my feet and wondering if it was too late to quit the program. Had I not told the internet I was going to do it, I just may have. That said, the widowmaker squats were never too terribly challenging: they were just additional suck on top of the suck. For me, the 5x5/3/1 squats were always more of a nut kick. The biggest thing is the fact it’s a mandatory 6 day per week program. You really just never get a break, and have to be totally locked in.
Next is Super Squats. And what had these last 3 programs shake out in terms of “hardness” for me was no longer about what they did to me physically but mentally. Super Squats was definitely my first real “gut check” in training at the tender age of 21, and it absolutely and totally re-wrote what effort and intensity meant in my mind, but it didn’t break me as hard as the next 2 programs did. But it DID break me physically in many ways. I tore my hamstring on my second run of it and had to do a combination of “Super Good Mornings” and going from 20 rep squats to 30 rep squats (yeah, that was fun), and the 3rd time I did it my elbow and hip were in such complete agony when it was done I had to spent a training cycle undoing the damage of the program. The first time I did it, I developed such bad anxiety about squatting in general that I could feel my heart race before I even started my 5x5 squat return program. But, ultimately, it will always be “just” one set of squats to get through. You only need to unrack the bar one time, and after that, you basically fight until you die. I think failing the squats is worse than succeeding, because you spend the next 48 hours obsessing over it, but that, in turn, really teaches you about finding ways to overcome.
Deep Water Beginner is the penultimate. I told you my story about wanting to sell all my lifting equipment from the final squat workout. While Super Squats gives you anxiety from workout to workout, Deep Water gives you 13 days and 23 hours of anxiety, because you just start that countdown timer as soon as you rack the bar from the 10th set of squats until the next squat workout, knowing you SOMEHOW have to shave off 1 minute of rest from last time. And even the “easy” workout suck because you’re so sore from the hard workouts. But the worst part is, unlike Super Squats, you have to unrack that bar TEN TIMES. That means you make the decision to do it 10 times, which is to say that, at any point, you could walk away and stop doing this to yourself. At least, with Super Squats, once the bar is unracked you’re pretty much locked in. But you could finish set 4 of 10 of Deep Water and just decide “nope, f**k this, not today” and walk away. So you have to KEEP forcing yourself to do more and more sets when you absolutely in no way want to do it.
…which is what makes Intermediate even worse. Whereas beginner says “take away 1 minute, now do it again”, intermediate says “Get 100 in 9 sets, now get it in 8”…but it never says HOW. No: that’s up to YOU to decide. This is the equivalent of back in the day when your dad would tell you to cut your own switch to get beaten with: you are being forced to decide HOW you will suffer. And you’ll spend those 13 days and 23 hours trying to figure out the combination that will suck the LEAST…but they will all suck. Also, since you’ve been doing Deep Water for 6 weeks before this, as you get through intermediate, you’re going to find out that your body is transforming but also destructing from the sheer brutality it’s been subjected to. It was a given that I was going to get an exertion headache after the squat workouts: I learned to take 2 excederin between sets 6 and 7 and drink a rockstar after the workout in order to chase it off as best as I could. I don’t even remember being sore any more when I did these programs. I don’t think I cared. I think it was more just the inevitability of the suck of the training.
Whelp, that was a fun trip down a psychotic memory lane, haha. Hope it’s helpful!