#33: Richard Schaal as Howard Arnell
Richard Schaal played Howard Arnell, Mary’s awkward, overly persistent former boyfriend. Howard’s relentless attempts to rekindle their relationship provided some of the show’s most endearingly cringeworthy moments. Schaal’s impeccable timing and nervous energy made Howard hilariously uncomfortable yet oddly sympathetic, embodying the kind of persistent suitor everyone dreads yet pities.
Howard’s hapless charm contrasted with Mary’s poised independence, highlighting how much she had outgrown him. Schaal’s comedic skill turned what could have been a throwaway character into a memorable part of Mary’s backstory, giving early episodes unexpected sparks of romantic chaos and offbeat humor.