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Wait, how or why would she even have been on Maher’s show in 1999, and which show was it?

I was curious about that to. I found this explanation from an obscure, liberally biased website:

After graduating in 1987 from Moorestown High School, O'Donnell attended Fairleigh Dickinson University, where she initially aspired to a career in the theater,[13] and did course work toward a B.A. in English and Communication.[17][18] She did not grow up as a strict Catholic, and came to a turning point during college when she found herself drinking excessively and engaging in promiscuity.[13] (She would later say of this period, "I know what it's like to live a life without principle.")[19] She became increasingly interested in both politics and religion.[16] She became an evangelical Christian, began preaching sexual abstinence and joined the College Republicans.
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Following college, O'Donnell went to work for Enough is Enough, a Washington, D.C.-based anti-pornography group.[19] She then spent two years working in conservative issue advocacy and for the Republican National Committee.[21] She served as a spokesperson for Concerned Women for America, a Conservative Christian political action group which opposes abortion,[22]and which seeks to apply biblical principles to other issues of public policy, as well.[19][23] In 1996, she attended the 1996 Republican National Convention in San Diego, California.[19]

O'Donnell then founded the Savior's Alliance for Lifting the Truth (SALT) in 1996 and served as its president.[19] The organization lobbied the U.S. Congress on moral issues[4] and focused on advocating chastity and other Christian values in the college-age generation.[24] O'Donnell made a number of high profile television appearances as a representative of SALT. In 1996 she appeared on MTV's show, Sex In The 90's, and advocated "sexual purity" when dealing with our "God given sexual desires". O'Donnell also publicly opposed masturbation, biblically equating it with adultery.[25] Two years later, O'Donnell appeared on Bill Maher's show Politically Incorrect, and argued that since America "took the Bible and prayer out of public schools" the country was "having weekly (school) shootings". She also remarked that the 1960s "sexual revolution" led to the AIDS epidemic.[26] She became a regular guest panelist on Maher's show, appearing in a total of 22 episodes. During another Politically Incorrect appearance, in a segment unaired until 2010, she described a previous experience with witchcraft, stating "I dabbled into witchcraft [but] I never joined a coven."

These statements came long after her religious conversion and while she was working for and founding conservative lobby groups. This is a non-issue.

Of course it’s a non issue, this is one the level of irrelevancy of the GWB DWI.

These statements came long after her religious conversion and while she was working for and founding conservative lobby groups. This is a non-issue.

I agree, but if there's anything 2008 taught us, it is to never underestimate the power of stupid voters in large numbers...