TITLE: When can two linear operators on a finite-dimensional space be simultaneously Jordanized?
QUESTION [43 upvotes]: IN a comment to Qiaochu's answer here it is mentioned that two commuting matrices can be simultaneously Jordanized (sorry that this sounds less appealing then "diagonalized" :P ), i.e. can be brought to a Jordan normal form by the same similarity transformation. I was wondering about the converse - when can two linear operators acting on a finite-dimensional vector space (over an algebraically closed field) be simultaneously Jordanized? Unlike the case of simultaneous diagonalization, I don't think commutativity is forced on the transformations in this case, and I'm interested in other natural conditions which guarantee that this is possible.
EDIT: as Georges pointed out, the statements that two commuting matrices are simultaneously Jordanizable is in fact wrong. Nevertheless, I am still interested in interesting conditions on a pair of operators which ensures a simultaneous Jordanization (of course, there are some obvious sufficient conditions, i.e. that the two matrices are actually diagonalizable and commute, but this is not very appealing...)

REPLY [14 votes]: I am 2 years late, but I would like to leave a comment, because for matrices of order 2 exists a very simple criterion.
Thm: If $A,B$ are complex matrices of order 2 and not diagonalizable then $A$ and $B$ can be simultaneously Jordanized if and only if $A-B$ is a multiple of the identity.
Proof: Suppose $A-B=aId$. 
Since $B$ is not diagonalizable then $B=RJR^{-1}$, where $J=\left(\begin{array}{cc}
b & 1 \\ 
0 & b\end{array}\right)$
Thus, $A= RJR^{-1}+aId=R(J+aId)R^{-1}=R\left(\begin{array}{cc}
b+a & 1 \\ 
0 & b+a\end{array}\right)R^{-1}$. Therefore $A$ and $B$ can be simultaneously Jordanized.
For the converse, let us suppose that $A$ and $B$ can be simultaneously Jordanized.
Since $A$ and $B$ are not diagonalizable then $A=RJ_AR^{-1}$ and $B=RJ_BR^{-1}$, where $J_A=\left(\begin{array}{cc}
a & 1 \\ 
0 & a\end{array}\right)$ and $J_B=\left(\begin{array}{cc}
b & 1 \\ 
0 & b\end{array}\right)$.
Therefore, $A-B=RJ_AR^{-1}-RJ_BR^{-1}=R(J_A-J_B)R^{-1}=R\left(\begin{array}{cc}
a-b & 0 \\ 
0 & a-b\end{array}\right)R^{-1}=(a-b)Id$. $\ \square$
Now, we can find many examples of matrices that commute and can not be simultaneously Jordanized.
Example: The matrices $\left(\begin{array}{cc}
a & 1 \\ 
0 & a\end{array}\right), \left(\begin{array}{cc}
b & -1 \\ 
0 & b\end{array}\right)$ are not diagonalizable and their difference is not a multiple of the identity, therefore they can not be simultaneously Jordanized. Notice that these matrices commute.