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| Season 5 | (Add Episode) |
| Episode # | Airdate | Title | Rating ![]() |
|
| 201 | 5x01 | 04/Jan/2000 | Cynthia Nixon | N/A |
| 202 | 5x02 | 05/Jan/2000 | Robbie Williams | N/A |
| 203 | 5x03 | 06/Jan/2000 | Richard Belzer | N/A |
| 204 | 5x04 | 10/Jan/2000 | Joe Montana | N/A |
| 205 | 5x05 | 11/Jan/2000 | Will Ferrell | N/A |
| 206 | 5x06 | 12/Jan/2000 | Ice Cube | N/A |
| 207 | 5x07 | 13/Jan/2000 | Michael Stipe | N/A |
| 208 | 5x08 | 17/Jan/2000 | Penelope Ann Miller | N/A |
| 209 | 5x09 | 18/Jan/2000 | Frankie Muniz | N/A |
| 210 | 5x10 | 19/Jan/2000 | Freddie Prinze Jr. | N/A |
| 211 | 5x11 | 20/Jan/2000 | Jerry Springer | N/A |
| 212 | 5x12 | 24/Jan/2000 | Selma Blair | N/A |
| 213 | 5x13 | 25/Jan/2000 | Peter Krause | N/A |
| 214 | 5x14 | 26/Jan/2000 | Jenny McCarthy | N/A |
| 215 | 5x15 | 27/Jan/2000 | David Arquette | N/A |
| 216 | 5x16 | 01/Feb/2000 | Jeff Bridges | N/A |
| 217 | 5x17 | 02/Feb/2000 | Focus on New Hampshire Special, special guest Bob Dole | N/A |
| 218 | 5x18 | 03/Feb/2000 | Jason Priestly | N/A |
| 219 | 5x19 | 14/Feb/2000 | Moby | N/A |
| 220 | 5x20 | 15/Feb/2000 | Dennis Farina | N/A |
| 221 | 5x21 | 16/Feb/2000 | Matthew Perry | N/A |
| 222 | 5x22 | 17/Feb/2000 | Ed McMahon | N/A |
| 223 | 5x23 | 22/Feb/2000 | Snoop Dogg | N/A |
| 224 | 5x24 | 23/Feb/2000 | Charlize Theron | N/A |
| 225 | 5x25 | 24/Feb/2000 | Rachael Leigh Cook | N/A |
| 226 | 5x26 | 28/Feb/2000 | Forest Whitaker | N/A |
| 227 | 5x27 | 29/Feb/2000 | Vin Diesel | N/A |
| 228 | 5x28 | 01/Mar/2000 | Tobey Maguire | N/A |
| 229 | 5x29 | 02/Mar/2000 | Ellen DeGeneres | N/A |
| 230 | 5x30 | 06/Mar/2000 | Neil Patrick Harris | N/A |
| 231 | 5x31 | 07/Mar/2000 | Kevin Pollak | N/A |
| 232 | 5x32 | 08/Mar/2000 | Bob Dole | N/A |
| 233 | 5x33 | 09/Mar/2000 | Garry Shandling | N/A |
| 234 | 5x34 | 13/Mar/2000 | Eddie Izzard | N/A |
| 235 | 5x35 | 14/Mar/2000 | Kim Delaney | N/A |
| 236 | 5x36 | 15/Mar/2000 | Wolf Blitzer | N/A |
| 237 | 5x37 | 16/Mar/2000 | George Wallace | N/A |
| 238 | 5x38 | 20/Mar/2000 | Chris Meloni | N/A |
| 239 | 5x39 | 21/Mar/2000 | Marla Sokoloff | N/A |
| 240 | 5x40 | 22/Mar/2000 | Eric Idle | N/A |
| 241 | 5x41 | 23/Mar/2000 | Leelee Sobieski | N/A |
| 242 | 5x42 | 27/Mar/2000 | John Lydon | N/A |
| 243 | 5x43 | 28/Mar/2000 | Joshua Jackson | N/A |
| 244 | 5x44 | 29/Mar/2000 | Triumph the Insult Comic Dog/Sam Donaldson | N/A |
| 245 | 5x45 | 30/Mar/2000 | Jimmy Smits | N/A |
| 246 | 5x46 | 10/Apr/2000 | Roger Daltrey | N/A |
| 247 | 5x47 | 11/Apr/2000 | Ben Stein | N/A |
| 248 | 5x48 | 12/Apr/2000 | Patrick Stewart | N/A |
| 249 | 5x49 | 13/Apr/2000 | David Alan Grier | N/A |
| 250 | 5x50 | 17/Apr/2000 | Stanley Tucci | N/A |
| 251 | 5x51 | 18/Apr/2000 | Samantha Mathis | N/A |
| 252 | 5x52 | 19/Apr/2000 | Diamond Dallas Page | N/A |
| 253 | 5x53 | 20/Apr/2000 | Arlen Specter | N/A |
| 254 | 5x54 | 24/Apr/2000 | Hugh Hefner | N/A |
| 255 | 5x55 | 25/Apr/2000 | Kirsten Dunst | N/A |
| 256 | 5x56 | 26/Apr/2000 | Jeanne Tripplehorn | N/A |
| 257 | 5x57 | 27/Apr/2000 | Stephen Baldwin | N/A |
| 258 | 5x58 | 01/May/2000 | S. Epatha Merkerson | N/A |
| 259 | 5x59 | 02/May/2000 | Luke Wilson | N/A |
| 260 | 5x60 | 03/May/2000 | Julie Warner | N/A |
| 261 | 5x61 | 04/May/2000 | Eric Close | N/A |
| 262 | 5x62 | 08/May/2000 | Wendie Malick | N/A |
| 263 | 5x63 | 09/May/2000 | Jesse L. Martin | N/A |
| 264 | 5x64 | 10/May/2000 | Andy Richter | N/A |
| 265 | 5x65 | 11/May/2000 | Betty White | N/A |
| 266 | 5x66 | 15/May/2000 | Tracey Ullman | N/A |
| 267 | 5x67 | 16/May/2000 | Kyle MacLachlan | N/A |
| 268 | 5x68 | 17/May/2000 | Jane Leeves | N/A |
| 269 | 5x69 | 18/May/2000 | Michael Rapaport | N/A |
| 271 | 5x71 | 30/May/2000 | Laura Kightlinger | N/A |
| 272 | 5x72 | 31/May/2000 | NONE | N/A |
| 273 | 5x73 | 01/Jun/2000 | Sonja Christopher | N/A |
| 274 | 5x74 | 05/Jun/2000 | Penn and Teller | N/A |
| 275 | 5x75 | 06/Jun/2000 | Kelli Williams | N/A |
| 276 | 5x76 | 07/Jun/2000 | Michael Moore | N/A |
| 277 | 5x77 | 12/Jun/2000 | When the Elderly Go on TV with Al Greenwood | N/A |
| 278 | 5x78 | 13/Jun/2000 | Mark Curry | N/A |
| 279 | 5x79 | 14/Jun/2000 | Jimmy Kimmel & Adam Carolla | N/A |
| 280 | 5x80 | 15/Jun/2000 | Julie Brown | N/A |
| 281 | 5x81 | 19/Jun/2000 | Heather Donahue | N/A |
| 282 | 5x82 | 20/Jun/2000 | Joe Lockhart | N/A |
| 283 | 5x83 | 21/Jun/2000 | Freddie Prinze Jr. | N/A |
| 284 | 5x84 | 22/Jun/2000 | Alicia Silverstone | N/A |
| 285 | 5x85 | 26/Jun/2000 | Cheri Oteri | N/A |
| 286 | 5x86 | 27/Jun/2000 | Jeff Probst | N/A |
| 287 | 5x87 | 28/Jun/2000 | Richie Sambora | N/A |
| 288 | 5x88 | 29/Jun/2000 | John C. Reilly | N/A |
| 289 | 5x89 | 10/Jul/2000 | Anna Paquin | N/A |
| 290 | 5x90 | 11/Jul/2000 | J. K. Simmons | N/A |
| 291 | 5x91 | 12/Jul/2000 | Famke Janssen | N/A |
| 292 | 5x92 | 13/Jul/2000 | Billy Crudup | N/A |
| 293 | 5x93 | 17/Jul/2000 | Shawn Wayans & Marlon Wayans | N/A |
| 294 | 5x94 | 18/Jul/2000 | Halle Berry | N/A |
| 295 | 5x95 | 19/Jul/2000 | Fourth Anniversary Special | N/A |
| 296 | 5x96 | 20/Jul/2000 | Al Roker | N/A |
| 297 | 5x97 | 24/Jul/2000 | Peter Fonda | N/A |
| 298 | 5x98 | 25/Jul/2000 | Joe Eszterhas | N/A |
| 299 | 5x99 | 26/Jul/2000 | Jennifer Beals | N/A |
| 300 | 5x100 | 31/Jul/2000 | Mo Rocca, Vance DeGeneres | N/A |
| 301 | 5x101 | 01/Aug/2000 | Republican National Convention coverage | N/A |
| 302 | 5x102 | 02/Aug/2000 | RNC coverage | N/A |
| 303 | 5x103 | 03/Aug/2000 | RNC coverage | N/A |
| 304 | 5x104 | 04/Aug/2000 | RNC, Peter Jennings | N/A |
| 305 | 5x105 | 15/Aug/2000 | Democratic National Convention coverage | N/A |
| 306 | 5x106 | 16/Aug/2000 | DNC coverage | N/A |
| 307 | 5x107 | 17/Aug/2000 | DNC coverage | N/A |
| 308 | 5x108 | 18/Aug/2000 | DNC coverage | N/A |
| 309 | 5x109 | 22/Aug/2000 | Jeremy Piven | N/A |
| 310 | 5x110 | 23/Aug/2000 | Slash | N/A |
| 311 | 5x111 | 24/Aug/2000 | Vincent D'Onofrio | N/A |
| 312 | 5x112 | 05/Sep/2000 | Donal Logue | N/A |
| 313 | 5x113 | 06/Sep/2000 | Greg Kinnear | N/A |
| 314 | 5x114 | 07/Sep/2000 | Spinal Tap | N/A |
| 315 | 5x115 | 11/Sep/2000 | Joe Mantegna | N/A |
| 316 | 5x116 | 12/Sep/2000 | Eugene Levy | N/A |
| 317 | 5x117 | 13/Sep/2000 | Lennox Lewis | N/A |
| 318 | 5x118 | 14/Sep/2000 | Joe Lieberman | N/A |
| 319 | 5x119 | 18/Sep/2000 | Ryan Phillippe | N/A |
| 320 | 5x120 | 19/Sep/2000 | Jamie Lee Curtis | N/A |
| 321 | 5x121 | 20/Sep/2000 | Barenaked Ladies | N/A |
| 322 | 5x122 | 21/Sep/2000 | Jamie Foxx | N/A |
| 323 | 5x123 | 25/Sep/2000 | Jonathan Katz | N/A |
| 324 | 5x124 | 26/Sep/2000 | Bill Goldberg | N/A |
| 325 | 5x125 | 27/Sep/2000 | Sylvester Stallone | N/A |
| 326 | 5x126 | 28/Sep/2000 | Tony Danza | N/A |
| 327 | 5x127 | 02/Oct/2000 | Dean Cain | N/A |
| 328 | 5x128 | 03/Oct/2000 | Ashton Kutcher | N/A |
| 329 | 5x129 | 04/Oct/2000 | Jewel | N/A |
| 330 | 5x130 | 05/Oct/2000 | Ralph Nader | N/A |
| 331 | 5x131 | 16/Oct/2000 | Alice Cooper | N/A |
| 332 | 5x132 | 17/Oct/2000 | Christian Slater | N/A |
| 333 | 5x133 | 18/Oct/2000 | Joshua Jackson | N/A |
| 334 | 5x134 | 19/Oct/2000 | Brendan Fraser | N/A |
| 335 | 5x135 | 23/Oct/2000 | Kevin James | N/A |
| 336 | 5x136 | 24/Oct/2000 | Jeff Garlin | N/A |
| 337 | 5x137 | 25/Oct/2000 | Posh Spice & Baby Spice | N/A |
| 338 | 5x138 | 26/Oct/2000 | Steven Weber | N/A |
| 339 | 5x139 | 30/Oct/2000 | Brett Butler | N/A |
| 340 | 5x140 | 31/Oct/2000 | David Frost | N/A |
| 341 | 5x141 | 01/Nov/2000 | Phil Donahue | N/A |
| 342 | 5x142 | 02/Nov/2000 | Michael Richards | N/A |
| 343 | 5x143 | 06/Nov/2000 | Arlen Specter | N/A |
| 344 | 5x144 | 07/Nov/2000 | Indecision 2000 Choose and Loose | N/A |
| 345 | 5x145 | 08/Nov/2000 | Richard Belzer | N/A |
| 346 | 5x146 | 09/Nov/2000 | Michael Moore | N/A |
| 347 | 5x147 | 13/Nov/2000 | Adam Sandler | N/A |
| 348 | 5x148 | 14/Nov/2000 | Patricia Arquette | N/A |
| 349 | 5x149 | 15/Nov/2000 | Adam Sandler | N/A |
| 350 | 5x150 | 16/Nov/2000 | Rhys Ifans | N/A |
| 351 | 5x151 | 20/Nov/2000 | Tales of Survival with Vance DeGeneres | N/A |
| 352 | 5x152 | 27/Nov/2000 | John Goodman | N/A |
| 353 | 5x153 | 28/Nov/2000 | Laura San Giacomo | N/A |
| 354 | 5x154 | 29/Nov/2000 | Billy Campbell | N/A |
| 355 | 5x155 | 30/Nov/2000 | Anthony Clark | N/A |
| 356 | 5x156 | 04/Dec/2000 | Thomas Gibson | N/A |
| 357 | 5x157 | 05/Dec/2000 | Faith Ford | N/A |
| 358 | 5x158 | 06/Dec/2000 | Chris O'Donnell | N/A |
| 359 | 5x159 | 07/Dec/2000 | John Goodman | N/A |
| 360 | 5x160 | 11/Dec/2000 | Ira Glass | N/A |
| 361 | 5x161 | 12/Dec/2000 | Greta Van Susteren | N/A |
| 362 | 5x162 | 13/Dec/2000 | Indecision 2000 Special | N/A |
| 363 | 5x163 | 14/Dec/2000 | Wolf Blitzer | N/A |
| 364 | 5x164 | 18/Dec/2000 | Marla Sokoloff | N/A |
| 365 | 5x165 | 19/Dec/2000 | Marisa Tomei | N/A |
| 366 | 5x166 | 20/Dec/2000 | Jeri Ryan | N/A |
| 367 | 5x167 | 21/Dec/2000 | Gillian Anderson | N/A |
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