Why is it that no one seems to embrace Halloween costumes quite like daytime talk show hosts? Sometimes they’re classic, other times they’re whimsical, and often they’re topical. But, for some reason, they are pretty much always funny, whether they’re intended to be or not. After the jump, we’ve collected some of our favorite silly Halloween getups, from Martha Stewart as Medusa to Regis in Susan Boyle drag to Ellen DeGeneres as a knocked-up J. Lo. Tell us who you think has done the best dress-up job year after year in the comments so we can crown a winner.
Ghostly Equestrian, 2009 Eat your heart out, Tim Burton!
Glampire, 2007 Always ahead of the curve, Martha was doing the vampire thing three years ago.
Medusa, 2008 This one is either a sign that Martha has a good sense of humor or proof that she’s totally oblivious. Either way, bold!
U.S. Presidents, 2008 Of course, Hasselbeck picks Reagan. But who couldn’t love Barbara Walters as George Washington and Whoopi as FDR? And can we discuss for a moment the wonderfulness of Sherri Shepherd as a leggy Lincoln on the penny? Brilliant.
Famous Vampires, 2009 These are all fantastic in their own way — despite lagging behind Martha by two whole years. Our favorite has to be the octogenarian Walters dressed to go to True Blood‘s Fangtasia.
Movie Characters, 1999 Barbara seems to be doing Cruella Deville, but Joy is truly inspired as The Birds‘s Melanie Daniels.
Horror Stars, 2005 Anyone want to take bets on how thrilled Joy — as a devil doll from the Chucky movies was to sit next to a bloodied Elisabeth (as Marion Crane from Psycho)?
Regis and Kelly
Kid Rock and Pam Anderson, 2003 Unfortunately, this one hasn’t aged well…
Simon Cowell and Paula Abdul, 2006 Alas, another pairing that is no more.
Jon and Kate Gosselin, 2009 These two were already on the train to Splitsville by the time last year’s Halloween episode aired. But check out Regis in Ed Hardy. Now that’s hot.
Susan Boyle and Lady Gaga, 2009 Last year, Regis and Kelly pulled off several costume changes. Even better than Jon and Kate, in our humble opinion, was the Reg as Susan Boyle and Kelly as the inimitable Lady Gaga.
The Wizard of Oz, 2009 Think Rosie’s former View colleagues were jealous, seeing her as a hilarious Glinda the Good Witch to Rachael’s Dorothy?
King Kong, 2008 Yup, that’s Rachael as Fay Wray. So who but her husband John Cusimano could play King Kong?
Who Framed Roger Rabbit?, 2010 In this year’s Halloween episode, set to air next Friday, Rachael will be the sexy Jessica Rabbit to John’s Roger. What’s with this hot lady-with-animal thing they’ve got going?
Pregnant Jennifer Lopez, 2007 This is all kinds of wonderful, totally speaks for itself, and may be the only time we’ve ever seen Ellen in a dress.
Change Mariachi, 2008 Okay, so the official costume — for an episode that aired just days before Barack Obama won the presidency — was simply “Change.” But I don’t think we can deny the mariachi inspiration here.
Ellen on the Cover of O, 2009 Donned in anticipation of her actual O cover, which came out a few weeks later.