I think I finally have a solution for all cases, thanks to the guidance from the other answers. To simplify the math, recenter the problem so the center of the circle is at the origin. We can fix the results afterwards to fit the original problem. Start with a general parabola and its slope:
$$\begin{align}
y&=-ax^2+c \tag{1}\label{1} \\
\frac{dy}{dx}&=-2ax
\end{align}$$
And the circle and its slope:
$$\begin{align}
y&=\sqrt{r^2-x^2} \tag{2}\label{2} \\
\frac{dy}{dx}&=\frac{-x}{\sqrt{r^2-x^2}}
\end{align}$$
If the two curves touch but do not cross, it must happen in the range $0 \le x < r$, because at $x=r$, the slope of the circle is undefined (where our parabola's never is), and after that the circle has no value. Similarly, we can say the range for $y$ is $0 \le y \le r$.
At the point of intersection, the parabola and the circle are tangent to one another (their slopes are equal), so:
$$\begin{align}
-2ax&=\frac{-x}{\sqrt{r^2-x^2}}\\
\Rightarrow x&=\sqrt{r^2 - \frac{1}{4a^2}}
\end{align}$$
Substituting for $x$ in $\eqref{2}$ yields:
$$y=\frac{1}{2a}$$
Now considering our upper bounds on $y$, we can say:
$$\begin{align}
\frac{1}{2a} & \le r\\
\Rightarrow a & \ge \frac{1}{2r}
\end{align}$$
Now to get the parabola in terms of velocities and gravity, combine the $x(t)$ and $y(t)$ representations (not shown) to get:
$$y=-\frac{g}{2v_x^2}x^2+\frac{v_y^2}{2g}$$
By comparison to $\eqref{1}$, we can say:
$$a=\frac{g}{2v_x^2}, c=\frac{v_y^2}{2g}$$
And since we have a bounds on $a$, we can conclude:
$$\begin{align}
\frac{g}{2v_x^2} & \ge \frac{1}{2r} \\
\Rightarrow v_x & \le \sqrt{rg}
\end{align}$$
This constraint defines a set of minimal solutions for a parabola which grazes the bounds of the circle without falling inside it, nor passing clear over it. (There is also a set of solutions which touch the circle at its apex ($x=0,y=r$) but which are "wider" than necessary.)
If $v_x=\sqrt{rg}$, the solution will touch the top of the circle with the minimum possible $v_y$. If $v_x \lt \sqrt{rg}$ (while still greater than zero, of course), the solution will touch the circle twice, once going up and once going down, and arc over the top of the circle in between.
Knowing that, we can get back to solving for $v_y$. Substituting $x$ and $y$ found above into $\eqref{1}$ yields:
$$c=\frac{4a^2r^2+1}{4a}$$
Now substitute $c$ and $a$:
$$v_y=\sqrt{ \frac{g^2r^2}{v_x^2} + v_x^2 }$$
But because we re-centered the problem, what this really gives us is our desired $v_y$ at the circle's midpoint (not from our launch point). Correcting for this is the relatively simple exercise of using the time-domain functions to find the time $t$ at which $y(t)=-r$ and then the velocity at that time.