Cassandra Cain is a tricky character to draw, and I wonder if that was her downfall. Garbed almost entirely in black with no visible facial features, this Batgirl could only be effectively handled through body language and extreme contortions of her head/mask. Original series artist Damion Scott set the tone, with an exaggerated style much too broad to serve on a standard Batman Family title, but necessary to convey Cain's personality through the suit. James Jean, the acclaimed cover painter for Fables, had a surprisingly long run on Batgirl as well. I never realized, because Jean never "got" the character visually, offering one off-flavor cover after another. Flashy work by some Wildstorm artists fared somewhat better, but it was a late series run by Tim Sale that allowed Cassandra Cain a brief return to form.
A lot of Damion Scott's covers were awful, and there's no shortage of middling art from No Man's Land, guest appearances and obligatory crossovers. There are also some solid pieces that didn't quite capture the spirit of Cassandra Cain, like a forgotten book co-starring Dark Horse Comics' Ghost, or the relatively recent Batgirl mini-series that proved a swan song. Below are what I feel are the best representations of the Cassandra Cain Batgirl, which (unusually) means that every example is from the ongoing series in which she starred.
10) Batgirl #71 (February, 2006)
Stalking her mother Lady Shiva's pupils through the highly contrasting snow.
9) Batgirl #55 (October, 2004)
The only James Jean cover to capture to any strong degree the proper body language.
8) Batgirl #25 (April, 2002)
One of Scott's weaknesses was pumping up the breasts on Cain's slight frame, but the aggressive posture and determination make up for the peep show.
7) Batgirl #41 (August, 2003)
The one instance where Jean cut loose, playing to his strength and forcing Cain to tag along. This one reflects the naïveté and yearning for connection Batgirl hid under her coarse exterior.
6) Batgirl #23 (February, 2002)
Cassandra Cain was more Batman than Batman, a genuinely creepy creature of the night.
5) Batgirl #73 (April, 2006)
Final, lethal combat against her absentee and homicidally psychotic mother. Tim Sale shows how to end a series.
4) Batgirl #14 (May, 2001)
I was never comfortable with Scott's sensuality, as Cassandra Cain always came across as very young and innocent for a highly trained assassin, but the mystique works here like gangbusters.
3) Batgirl #4 (July, 2000)
The littlest hit girl, years before Kick-Ass, and still fairly unique in fiction.
2) Batgirl #2 (May, 2000)
Can't recall hearing such a bold request phrased so intriguingly.
1) Batgirl #1 (April, 2000)
Hardly a masterpiece, but it's the only debut issue cover that fully worked.