Please note that the following was never said by the following Rabbis, rather it’s answered in their style and is meant in pure jest.
This was heavily influenced by a famous chain email on why the chicken crossed the road, according to celebrities.
Why does it say “the chicken” and then the road, rather than the road, which forms the foundation and not the chicken? To show us that (*thumb drop*) ONLY IF there is a chicken, can there be a road! Uh!
R’ Akiva Tatz
The chicken crossing the road shows that the chicken is acknowledging it’s roost (sic). The chicken is a mirror image of the road. The road is actually crossing and the chicken is really is the analogy of the road! Only in the next world when everything is clearer will we see how a road can cross.
Rabbi Benzion Shafier
We see from here that the chicken crossed the road, but friends, that-is-the-point. When I cross a road, do I think “oh gee, I really need to worry about getting to the other side?” Usually we look at the trees, the rocks, and easily get distracted. All of these distractions prevent US from getting to the other side! And once it’s too late and we’re hit by a passing car on the road, I can no longer get to the other side, as by then it’s too late. I am dead as a doornail, and can no longer get up.
R’ Elchonan Wasserman
The chicken, you see, is a reflection of the road. The chicken walks where the road wills it to walk.
The chicken crossing the road is a reflection on ourselves. When we see the chicken crossing the road to get to the other side we see ourselves crossing this world to get closer to Shamayim, which is on the other side.
(*Playing Guitar*) Let me tell you a story, let me te-e-e-ll you a story. Let me tell you a story about a holy chicken!!!! A Ho-o-o-oly chicken! A holy chicken, my beautiful friends, that was at a crossroads and didn’t know whe-e-ere to go. The holy chickenover said to himself, “If I don’t move forward in either direction, then I will never grow.” He therefore chose a direction and crossed it to get to the o-o-o-therrrrr side……
R’ Avraham Schorr
The whole idea, of the chicken crossing the road, is a great Nisayon for us! This is the greatest Milchamah of our days (*stroking Payos*)! One should set up a barrier between himself and the road RT”L! Amalek will tell you that you don’t have to worry about the chicken crossing the road! Our Rabbonim say that there will be a 3rd world war when that chicken crosses that road!
(*Shaking Fist*) The chicken is a cancer. And you cannot co-exist with a cancer. We therefore tell these chickens to cross the road to it’s 22 acres of land – Gd bless them – and leave us with our one little acre. Chickenim – Hachutzah! I want them out.
The chicken crossed the road because it didn’t know that there was a crosswalk. Crosswalks only existed on the other side, so it was impossible for the chicken to know otherwise until he reached the other side. Therefore, the chicken was flawed.
One should be very careful to let a chicken cross the road and to help him out. It’s seen in the Zohar that the angels ask Gd, “when will it be that a chicken will be free to cross the road without any questions?” It’s also seen that chicken somehow relates to Gashmiyus. If one obsesses over the chicken he will be reincarnated into one RT”L! Therefore one should be careful to put aside his haughtiness, and aid a chicken in his journey, and all will be good.
Why did the Lubavitcher cross the road? To try and put tfillin on the chicken…