Christmas Duets; Present day artists combined with past days artists. Which couple do you suggest?

I wouldn’t mind hearing Adam Levine from Maroon 5 singing with Barbara Streisand singing The Holly and the Ivy.

Oh I thought you meant “Artist” artists…

I’d like to see Caravaggio mix it up with Thomas Kinkade.

I thought they did a pretty good job with the David Bowie/Bing Crosby mix of Little Drummer Boy.

I think another Bing Crosby collaboration, this time with Marilyn Manson, would be great if they did Mele Kalikimaki together.

One of my favorite holiday songs is “Baby It’s Cold Outside” sung by Leon Redbone and Zooey Deschanel.

Trying to come up with an answer, I considered Linda Rondstadt and Andy Williams, then I found one online!
(then I realized Linda is not really present day, dammit)

How about one with Elvis and Adele?

Elvis with Bon Scott, Jim Morrison and Michael Jackson, Frank Sinatra with Roy Orbison.

If you’re talking about creating a track where a modern artist “duets” with someone no longer living, I never liked that idea. It seems disrespectful IMHO, because the deceased singer can’t give consent to the musical partnership. Who’s to say that Elvis would want to duet with Kelly Clarkson if he were alive? Now, I do like it when a living, well-established artist sings with a new, up-and-coming singer (like the Leon Redbone/Zooey Deschanel partnership mentioned upthread—those two should do a holiday album together!).

Lady Gaga and Tony Bennet recently did a duet of The Lady is a Tramp that came out great. I could totally see them doing some Christmas songs, too.

My favorite is the one @Blondesjon mentioned, with David Bowie and Bing Crosby. For current-ish and current-ish Christmas duets, you can’t beat the Barenaked Ladies and Sarah McLachlan’s version of God Rest Ye Merry Gentlemen/We Three Kings.