First, note that your pictures don't actually convey the correct column vectors - the second vector should have $-b$ as its $x$-component, not its $y$.
But this isn't a very useful way of visualizing the situation anyway; a matrix isn't just an assemblage of vectors. The "right" way to think about matrices is as a transformation. A $2\times 2$ matrix is a transformation from $\mathbb{R}^2$ to $\mathbb{R}^2$. In this case, the particular matrix you describe has a very nice interpretation as a transformation: it's a rotation and a scaling together. To be specific, the matrix $\left(\begin{array}{cc}\cos(\theta) & -\sin(\theta)\\\sin(\theta) & \cos(\theta)\end{array}\right)$ is a counterclockwise rotation by the angle $\theta$. Conveniently, the vector $(\cos(\theta), \sin(\theta))$ is a unit vector inclined at an angle $\theta$ from the $x$-axis. So if $\mathbf{u}$ is a unit vector, $\tau(\mathbf{u})$ is the transformation of rotating counterclockwise by the angle $\mathbf{u}$ makes with the $x$-axis.
If $\mathbf{a}$ is not a unit vector, then it's $||\mathbf{a}||\mathbf{u}$ for some unit vector $\mathbf{u}$. $\tau(\mathbf{a})$ turns out to be $||\mathbf{a}||\tau(\mathbf{u})$ (I'll let you check that). So we get a scaling by a factor of $||\mathbf{a}||$ as well.
For example, if $\mathbf{a} = (1,1)$ (so $a = b = 1$), then $\tau(\mathbf{a})$ is a counterclockwise rotation by $45^{\circ}$, followed by a stretching by a factor of $\sqrt{2}$.
Note: above, I've written vectors in the format $(a,b)$ rather than as column vectors; that's just for my convenience.