Update!

Five Super-Surprising Star Couples—Not Counting Brenda Song and Trace Cyrus

Kimberly Stewart and Benicio Del Toro's baby news has us reeling—and thinking of other seemingly random duos

By Joal Ryan Aug 24, 2011 12:00 PMTags
Brenda Song, Trace CyrusMichael Buckner/Getty Images

If you told us Brenda Song and Miley Cyrus were friends, we'd say, "Of course. Disney Channel connection and all that."

But when news leaked Song and Cyrus' brother, Trace Cyrus, were pregnant, we went… Well, we did a spit take.

In this rundown originally published last April when new parents Kimberly Stewart and Benicio Del Toro shocked with their own baby announcement, we recall five Hollywood couplings that also caught us off guard:

Christopher Hall

1. Tom Cruise and Katie Holmes: No matter how long they're together—and they've been at it six years now, folks—they make you go, "Really?! The World's Biggest Movie Star and Joey from Dawson's Creek—really?!" Really.

Steve Granitz/Getty Images

2. Jesse James and Sandra Bullock: The garage guy and the good girl. They said it'd never last. And, um, well, they were right. 

3. Jake Gyllenhaal and Taylor Swift: Sure, they're both young, cute and single—or, in the 30-year-old Gyllenhaal's case, young-ish, cute and single. But be honest: Until they were snapped together last fall, did you have any idea they would pool their collective talents (however briefly)?

ZumaPress.com, Nancy Kaszerman/ZumaPress.com

4. Kenny Chesney and Renée Zellweger: There's nothing necessarily shocking about a country crooner and a movie queen. (See: Keith Urban and Nicole Kidman.) But there is something totally shocking about a country crooner and a movie queen marrying within five months of meeting (and then splitting four months later).

KIM KULISH/AFP/Getty Images

5. Michael Jackson and Lisa Marie Presley: Name any jaw-dropping couple from any time—Antony and Cleopatra, Arthur Miller and Marilyn Monroe, etc.—and we doubt you'll come up with one that seems more out of the blue, in a perfect sort of way, than the King of Pop wedding the King of Rock's daughter. (Well, all right, maybe Elvis fan Nicolas Cage wedding Presley…)

(Originally published April 12, 2011, at 5:00 a.m. PT)