1999
| Issue date | Cover subject | Type of cover | Artist |
|---|---|---|---|
| 1/2/1999 | *Diane Sawyer and Barbara Walters of ABC News *Members of the Florida State and Tennessee football teams (6 covers) |
Photograph | |
| 1/9/1999 | "Winter Preview", featuring Eddie Murphy of The PJ's, Jennifer Grey of It's Like, You Know..., John Larroquette of Payne, and the title character of Dilbert | Photo montage | Murphy: Archive Photos/Express News; Larroquette: Tony Esparza for CBS; Dilbert: United Features Syndicate |
| 1/16/1999 | *Rick Schroder of NYPD Blue Inset: Katie Holmes of Dawson's Creek *Mike Tyson |
Photograph | |
| 1/23/1999 | "The 50 Funniest TV Moments of All Time", featuring Carol Burnett, Lucille Ball, and Jerry Seinfeld | Photo montage | |
| 1/30/1999 | "The TV Guide Awards" preview, featuring Jenna Elfman, Bill Cosby, Calista Flockhart, Michael J. Fox, Christina Applegate, Jimmy Smits, Roma Downey, and Tim Allen | Photo montage | Elfman: Bob D'Amico for ABC; Cosby: Tony Esparza for CBS; Flockhart: Davis Factor for Fox; Fox: Timothy White for ABC; Applegate: Sam Jones for NBC; Smits: Gwendolen Cates for ABC; Downey: Cliff Lipsom for CBS; Allen: Kimberly Butler for ABC |
| 2/6/1999 | George Clooney of ER | Photograph | CPI |
| 2/13/1999 | *Colm Feore of Storm of the Century *NASCAR preview, featuring drivers Jeff Gordon, Dale Jarrett, Mark Martin, and Rusty Wallace (separate covers) |
*Feore: illustration *NASCAR: photograph |
*Feore: Matt Mahurin for TV Guide *NASCAR: Marc Royce for TV Guide |
| 2/20/1999 | Patricia Heaton, Ray Romano, & Brad Garrett of Everybody Loves Raymond, recreating the 9/7/1968 Family Affair cover | Photograph | Darien Davis |
| 2/27/1999 | Tina Majorino & Martin Short of Alice in Wonderland | Photo montage | |
| 3/6/1999 | The cast of 7th Heaven | Photograph | |
| 3/13/1999 | *Jenna Elfman & Matthew McConaughey of the film EDtv *Chamique Holdsclaw of the Tennessee Volunteers |
Photograph | |
| 3/20/1999 | "Oscar preview", featuring nominees Gwyneth Paltrow, Tom Hanks, Nick Nolte, and Meryl Streep | Photo montage/word art | |
| 3/27/1999 | Wrestlers Stone Cold Steve Austin, The Rock, Sable, and Mankind appearing on 4 separate covers | Photograph | Uli Rose for TV Guide |
| 4/3/1999 | Bender of Futurama | Illustration | |
| 4/10/1999 | Lucy Lawless of Xena: Warrior Princess & Jeri Ryan of Star Trek: Voyager | Photograph | Kate Garner for TV Guide |
| 4/17/1999 | David Duchovny of The X-Files | Photograph | Cliff Watts for TV Guide |
| 4/24/1999 | *"Sweeps Preview", featuring Brandy and Diana Ross of Double Platinum, Heather Locklear of Melrose Place, and Garth Brooks (national) *Philadelphia Flyers players John LeClair, Rod Brind'Amour, Eric Lindros, and Mark Recchi (separate covers) |
*Sweeps: photo montage *Flyers: photograph |
|
| 5/1/1999 | *Calista Flockhart of Ally McBeal *1999 Kentucky Derby preview, featuring General Challenge and jockey Gary Stevens |
Photograph | |
| 5/8/1999 | *Camryn Manheim of The Practice *A salute to John Elway (4 covers) |
Photograph | |
| 5/15/1999 | The film Star Wars: Episode I – The Phantom Menace (4 covers forming a montage) *Jake Lloyd as Anakin Skywalker with C-3PO and R2-D2 *Liam Neeson as Qui-Gon Jinn with Darth Maul *Darth Maul with Ewan McGregor as Obi-Wan Kenobi *Natalie Portman as Queen Padme Amidala |
Illustration | |
| 5/22/1999 | Patricia Richardson & Tim Allen of Home Improvement, with a 1992 cast photo in inset | Photograph | |
| 5/29/1999 | *The finale of Star Trek: Deep Space Nine (4 newsstand covers) ** Avery Brooks ** Nana Visitor and René Auberjonois ** Michael Dorn, Armin Shimerman, and Nicole deBoer ** Alexander Siddig, Colm Meaney, and Cirroc Lofton *The cast of Just Shoot Me (subscriber cover) |
Photograph | |
| 6/5/1999 | *Ricky Martin (2 covers) *Members of the Buffalo Sabres and Colorado Avalanche (8 covers) |
Photograph | |
| 6/12/1999 | Characters Jabba the Hutt, Jar Jar Binks, Watto, and Boss Nass from the film Star Wars: Episode I – The Phantom Menace (separate covers) | ||
| 6/19/1999 | *Laura Prepon, Topher Grace, and Danny Masterson of That '70s Show *Wrestler Sable |
Photograph | |
| 6/26/1999 | Pamela Anderson Lee of V.I.P. | ||
| 7/3/1999 | "The 50 Greatest Commercials of All Time", featuring Life cereal's Mikey, Taco Bell chihuahua Gidget, Michael Jordan, and the Energizer Bunny | Photo montage | |
| 7/10/1999 | Chris Rock | Photograph | Frank W. Ockenfels |
| 7/17/1999 | *Dennis Franz of NYPD Blue *NASCAR stars Bobby Labonte, Tony Stewart, Jeremy Mayfield, and Jeff Burton (separate covers) |
Photograph | |
| 7/24/1999 | "TV Confidential 2", featuring Madonna, Scott Baio, Susan Olsen, & Bob Eubanks | Photo montage | Olsen: ABC Photo Archive |
| 7/31/1999 | Remembering John F. Kennedy Jr. | Photograph | |
| 8/7/1999 | "TV's 16 Sexiest Stars", featuring David James Elliott of JAG and Alyssa Milano of Charmed (separate covers) | Photograph | Alberto Tolot for TV Guide |
| 8/14/1999 | *Wrestlers Kimberly Page, Kevin Nash, Randy Savage, and Sting (separate newsstand covers) *"TV's Macho Men", featuring Sammo Hung of Martial Law, Kevin Sorbo of Hercules: The Legendary Journeys, and Chuck Norris of Walker, Texas Ranger (subscriber cover) |
Photograph | *Page, Nash, and Savage: Frank W Ockenfels III for TV Guide; Sting: Darryl Estrine for TV Guide |
| 8/21/1999 | Cher | Photograph | |
| 8/28/1999 | NFL preview issue (34 regional covers) | Photograph | |
| 9/4/1999 | "Returning Favorites" issue, featuring David Duchovny of The X-Files, Jennifer Aniston of Friends, Ray Romano of Everybody Loves Raymond, Roma Downey of Touched by an Angel, D. L. Hughley of The Hughleys, and Katie Holmes of Dawson's Creek | Photo montage | Downey: Cliff Lipson for CBS; Hughley: George Lange for ABC |
| 9/11/1999 | Fall Preview | Word art | |
| 9/18/1999 | *Faith Hill *Sammy Sosa of the Chicago Cubs |
Photograph | |
| 9/25/1999 | *"The Best New Shows", featuring Shiri Appleby of Roswell, Jay Mohr of Action, Linda Cardellini of Freaks and Geeks, David Boreanaz of Angel, Sela Ward of Once and Again, and Rob Lowe of The West Wing (national) *Cleveland Browns players Lomas Brown, Orlando Brown, Antonio Langham, and Jamir Miller (separate regional covers) *New York Mets players Mike Piazza, Edgardo Alfonzo, Al Leiter, and Robin Ventura (separate regional covers) |
* "Best": photo montage *Browns and Mets: photograph |
Ward: Challenge Roddie for TV Guide; Lowe: Kevin Foley for NBC |
| 10/2/1999 | *Melissa Joan Hart of Sabrina, the Teenage Witch *Baseball playoff preview, featuring members of the Cleveland Indians, Arizona Diamondbacks, New York Yankees, Boston Red Sox, and Cincinnati Reds (20 separate covers) |
Photograph | |
| 10/9/1999 | Katie Couric of Today | Photograph | |
| 10/16/1999 | "TV's 50 Greatest Characters Ever!" featuring Cosmo Kramer, Mr. Spock, J. R. Ewing, and Mary Richards | Photo montage | |
| 10/23/1999 | *"Grownups are back!" featuring Billy Campbell and Sela Ward of Once and Again *Amanda Bynes of The Amanda Show(Ultimate Cable edition) |
Photograph | |
| 10/30/1999 | Characters from Pokémon (4 covers forming a montage) | Illustration | |
| 11/6/1999 | *Regis Philbin of Who Wants to Be a Millionaire *NBA preview, featuring Tim Duncan of the San Antonio Spurs and Kevin Garnett of the Minnesota Timberwolves (separate covers) |
Photograph | Philbin: Josef Astor for TV Guide |
| 11/13/1999 | Pierce Brosnan | Photograph | Cliff Watts for TV Guide |
| 11/20/1999 | *Celine Dion (national) *Remembering Walter Payton (Chicago area) *Members of the Portland Trail Blazers (4 regional covers) |
Photograph | |
| 11/27/1999 | Rosie O'Donnell of The Rosie O'Donnell Show | Photograph | |
| 12/4/1999 | Michael Jackson | Photograph | |
| 12/11/1999 | Amy Brenneman of Judging Amy | Photograph | Kate Garner for TV Guide |
| 12/18/1999 | The cast of Ally McBeal (foldout cover) | Illustration | Al Hirschfeld |
| 12/25/1999 | Dennis Haysbert, Eric Close, & Margaret Colin of Now and Again | Photograph | Stephen Danelian for TV Guide |
