As soon as Howard's next guest, Darrell Hammond, came into the studio, Howard pointed out that he looked "manorexic." Darrell responded that he stopped eating sugar and flour for a while in an attempt to lose weight and that the weight "fell off pretty fast" because of his diet. However, Darrell added that, since he doesn't want to get any thinner, he can see himself resorting back to his old eating habits and "getting fat again."
Darrell announced that he's currently in his eleventh season on "Saturday Night Live," but that he doesn't expect his run to go on much longer. Darrell also reported that he sometimes feels embarrassed that he hasn't landed a big movie deal or gotten his own sitcom like so many of his "SNL" alums have, but that he also enjoys working on the show a great deal. Darrell went on to say that, because he's been on "SNL" for so long, he has an accommodating work schedule, and that he earns "great money," which he acknowledged were great incentives for him to stay.
Howard pointed out that Darrell sometimes comes off as depressed to him, and Darrell admitted the fact that he doesn't have a woman in his life has been bringing him down as of late. Howard proceeded to read a list of the celebrities Darrell impersonates – including Al Gore, Rudy Giuliani, Jay Leno and Barney Fife – and Darrell did some of their voices. After Darrell also performed Artie's favorite impression of his, which is Darrell's Jesse Jackson, Howard wondered if Darrell would be interested in doing an hour-long program on Howard 100 that features just his impersonations. Darrell responded that, as long as Howard promoted the broadcast, he'd be willing to do it.
Darrell admitted that he had a cocaine problem years ago that lasted four months and that he developed it because he "was a drunk." This led Artie to comment that he could relate to Darrell's situation, before talking about his worst experience buying cocaine. Artie recalled that he was doing a sketch called "Babe Watch" for "Mad TV" at the time, and that he was in an elaborate pig costume for it. Artie then said that, between shoots, he left the lot to find his dealer, who asked what "kind of sh*t he was into" because he was still in full costume. Artie added that, after he explained to his dealer that he was on television and was getting ready to film a sketch, he ended up sniffing cocaine off a key through his prosthetic pig snout on his way back to the studio. Upon hearing Artie's story, Darrell noted that the most embarrassing thing he ever did while on cocaine was "trying to pick up Asian chicks" with $200 in quarters.
Because Darrell expressed interest in finding a woman, Robin wondered if Howard could have Beth fix him up with one of her friends. Howard responded that since Beth doesn't have many female friends that probably wouldn't be an option, but that he thought Penny Crone and Darrell would make a nice couple. Penny came into the studio and said that she finds Darrell "hot" on "SNL," before telling Howard that she wasn't married. However, Gary then entered the studio and asked who the man was that Penny introduced as her husband to him last week. Penny acknowledged that she knows a man whom she sometimes passes off as her spouse, but that they're not really married. Penny continued attempting to hit Darrell by sticking her fist into her mouth, but Howard noted he didn't think Darrell was into her.
Darrell brought up that he's performed in front of President Clinton, as well as both Bushes. Darrell added that he's sometimes paid for these routines, but that he usually does them because he's honored to be in the presence of the presidents, regardless of their politics. Darrell also admitted that he gets nervous when performing for such important people and noted that he recently made a joke in front of the first Pres. Bush about Dan Quayle never shooting anyone that he regretted making after the fact.