The only possible Jordan Normal forms for a rank $1$ matrix are
$$J_1= \left(\begin{array}{c|ccc}
c & 0 & \cdots & 0 \\ \hline
0 & 0 &\cdots &0\\
{\vdots} & \vdots& \ddots & \vdots\\
0 & 0 & \cdots & 0
\end{array}\right)
J_2= \left(\begin{array}{cc|ccc}
0 & 1 & 0&\cdots & 0 \\
0 & 0 & 0 &\cdots &0\\ \hline
0 & 0 & 0 & \ldots &0\\
{\vdots} & \vdots& \vdots & \ddots & \vdots \\
0 & 0 & 0 & \cdots & 0
\end{array}\right)$$
This makes the claim almost trivial: if $A$, $B$ are two rank one matrices, then
$$\text{tr}(A)=c_{A},\qquad \text{tr}(B)=c_{B} $$
where $c_A$, $c_B$ are either $0$ or the only non-zero eigenvalues of the two matrices. If $c_A=c_B$, the two matrices have the same normal form and hence are similar, otherwise they are not.
Without using the Jordan decomposition, one can notice that the kernel of a rank one operator $A$ has dimension $n-1$. Consider a basis of $\ker A=\langle v_2,\ldots, v_n \rangle$ and a linearly independent vector $v_1\not \in \ker A$. We can visualize the kernel of a matrix as the eigenspace of eigenvalue $0$. If there exists one non-zero eigenvalue, algebraic and geometric multeplicity of $0$ coincide. Let $c$ be $A$'s only non-zero eigenvalue. For dimensionality restrictions, we know that $c$'s eigenspace $V_c$ has dimension one. Since eigenspaces relative to different eigenvalues are in direct sum,
$$V=\ker A \oplus V_c$$
implying that $A$'s matrix is exactly $J_1$. This shows that if $\text{tr}(A)=c_A,~\text{tr}(B)=c_B$, with $c_A,c_B\neq 0$ then $A$ is similar to $B$ if and only if they have the same trace.
Now, if $A$ has only $0$ as an eigenvalue, then $A$'s characteristic polynomial is $x^n$. This shows that if $A,B$ are two rank one matrices such that $\text{tr}(A)=0,~ \text{tr}(B) \neq 0$ they are not similar, because their characteristic polynomials are different.
If $\text{tr}(A)=\text{tr}(B)=0$, the matrices are similar to two of the following kind:
$$A'= \left(\begin{array}{c|ccc}
0 & 0 & \cdots & 0 \\ \hline
a_1 & 0 &\cdots &0\\
{\vdots} & \vdots& \ddots & \vdots\\
a_n & 0 & \cdots & 0
\end{array}\right)
B'= \left(\begin{array}{c|ccc}
0 & 0 & \cdots & 0 \\ \hline
b_1 & 0 &\cdots &0\\
{\vdots} & \vdots& \ddots & \vdots\\
b_n & 0 & \cdots & 0
\end{array}\right)
$$
I cannot think of an elementary method to show that they are similar at the moment, I'll edit the post if something comes to mind.