I lived in Hollywood for several years, and worked for awhile at a neighborhood cafe on a major street. Waited on a good amount of celebs. Here are some of the better stories:
I sorta kinda introduced the rapper The Game to Al Pacino. The Game was a semi-regular for awhile. Pacino has young kids who were attending the private school down the street, and on graduation day he came in twice. In the morning, he joined his children's mother, Beverly D'Angelo (she played Ellen Griswold in the "Vacation" movies), for coffee, and The Game, having never met Pacino, told me to tell them that he would take care of their bill. The three of them proceeded to have a nice chat. My co-worker later told me that The Game recorded a song called "Breakfast with Al Pacino" ... Pacino came back for lunch with the kids--he told them if they didn't behave he was going to "take them to the dentist." An all-around surreal experience to say the least.
It was one of those rare days in LA where it absolutely pours down rain all day. It was our slow period, and I was the only server working, and it's very possible the place was totally empty. In walks a mysterious female in a trench coat, hat and glasses. She took my advice and ordered the chili. She had a soft, sultry voice that I knew sounded incredibly familiar, but she was disguised thoroughly enough that I couldn't be too sure. It wasn't until she handed me her credit card that I confirmed my suspicion. I'm certain my hand was shaking as I swiped the payment for Christina Hendricks. I told her that I loved her show, she thanked me ever so sweetly, and I melted. I might have actually pinched myself after she left.
Richard Simmons came in one day for take out. He was dressed as appropriately as you might hope, sequined animals on his shirt and all. He started making a bunch of racket, randomly shouting nonsensical things at customers and employees (e.g. a female co-worker emerged from the kitchen and Richard blurts out, "Oh my god, it's Snow White!"--she looked nothing like Snow White). His assistant tried reigning him in ("Okay, Richard..."), but you could tell he was used to this stuff. Simmons exited blowing kisses at everyone.
Norm Macdonald ordered like he was doing his act. "So...uh...what I want is, uh...one of these turkey burgers here, see? But, uh...instead of having like...a bun...you, uh...you wrap it in some lettuce. You uh...you ever hear of something like that?" All with a big shit-eating grin on his face. I was practically biting my lip to keep from cracking up.
I was a teenager when "American Beauty" and "American Pie" came out, and I thought Mena Suvari was awfully cute in a quirkier sort of way, but up close in real life, she was almost hard-to-look-at hot. I waited on Emily Blunt, Amy Adams, Julianne Hough, Erin Andrews, et al. All were beautiful even in scrubby diner attire, but Mena was tongue-on-the-ground stunning.
And a few non-serving stories:
I was attending a Halloween party thrown by friends of one of my roommates. It was at a nondescript apartment in the Valley. My roommate was dressed as Pee-Wee Herman, and this one girl was all about it. Like seriously into him. At one point, we were all getting our boogie on and she said to me, "It's fun to dance un-ironically." Anyway, she dropped some not-very-subtle hints his way, but he seemed very apprehensive for some reason. I guess he immediately recognized her, whereas it took me some time to connect the dots. It donned on me that she looked familiar, then I realized that I knew her from an ESPN web series. My friends then informed me she was one of the stars of "Parks and Rec" (one of the guys hosting the party had a really small role on the show). Turns out Aubrey Plaza was crushing on my buddy...and he did nothing about it (this same guy allegedly turned down a FFM threesome in London, so...yeah).
We were coming back from a Dodger game and stopped at our favorite corner store for some Swishers and beverages. Once in line, a well-dressed middle age cat came in looking like drunken death. It took a split second for me to register that Mel Gibson was standing there. Dude was L-I-T. He asked the cashier where he could find bottled water, and the guy was like, "Uh, right behind you, sir." I thought poor Mel was going to fall right through the cooler door when he turned around. It was hysterical, but I actually felt sorry for him. When we left the store, the car parked next to me was a BMW convertible with a model type who didn't look a day over 23 texting furiously in the passenger seat. We were just hoping not to see his totaled ride on the news the next day.
This wasn't in LA, but it might be my personal favorite celeb sighting story. I'm from Ohio, and me and a couple friends went for a day trip to this hippie college town where Dave Chappelle makes his residence. We went hiking, got some grub, etc. The whole day we made Dave-related cracks, holding out the distant hope that we might see him. We were getting ready to head out, but I had to take a severe leak before we hit the road. Coming out of a coffee shop, I almost bumped into a guy moseying down the street. I looked at him and did all I could to stifle my shock. It was M-F'in Chappelle himself. I said, "Hey," and he asked, "How's it goin?" And that was that. We burned a fat one in his honor on the ride home.