''Tis the Season to Be Merry'
Rachael Leigh Cook is practically Hallmark royalty. In her eighth movie for the network, the Minnesota native plays a love expert who can't manage to find romance in her own life — until she spends a magical holiday in Vermont. Despite being based on a story by Jen Kirkman, a stand-up comic who is a member of Chelsea Handler's posse, the film relies on a cookie-cutter formula. There's not a single scene that would make the naughty list. But if all you're looking for is cuteness for Christmas, Cook is still "all that." 7 p.m. Sunday, Hallmark
Few of us get a chance to see Shakespeare in the Park in winter. This documentary is the next best thing. Director Rudy Valdez follows the cast and crew of "Merry Wives," an all-Black production based on one of the Bard's classics. The daunting obstacles include rain, raccoons and, of course, the pandemic. But the heart of the film is how these creative folks are re-evaluating their priorities in the wake of George Floyd's death. 9 p.m. Monday, HBO
'Jim Gaffigan: Comedy Monster'
There's little evidence that the talented stand-up filmed his latest special in Minneapolis but that shouldn't dissuade you from enjoying this well crafted set. Gaffigan, who also directed, never mentions Hot Pockets, but he hits plenty of his signature topics including obesity and a disappointed wife. The edgiest bit comes when the comic dares to attack marching bands. Netflix starting Tuesday
'The Masked Singer Christmas Singalong'
If a bunch of creepy sports mascots began caroling outside your door, you'd be tempted to call the police. But fans of this unlikely hit will be tickled pink by this special in which former contestants warble holiday classics, including "Rudolph the Red-Nosed Reindeer." The two-hour episode also features bloopers and behind-the-scenes footage. 7 p.m. Wednesday, KMSP, Ch. 9
'The 44th Annual Kennedy Center Honors'
TV's most reliable holiday gift returns with tributes to Lorne Michaels, Joni Mitchell, Bette Midler, Berry Gordy and Justino Diaz. As a extra treat, David Letterman steps in as host, a duty he took seriously enough to trim his beard. Those in attendance praised the entertainment, particularly Stevie Wonder's tribute to his old Motown boss. But some reported that Paul Simon's version of "America" was so off-tune it might not even make the final cut. 8 p.m. Wednesday, WCCO, Ch. 4