If the name "Hollywood" sounds glamorous, you might be disappointed in Portland's Hollywood District, though there's nothing wrong with it. The area's only connection to movies is the fabulous old Hollywood Theatre; the area's original name was "Hollyrood" according to Wikipedia and was renamed to "Hollywood" after the theatre itself arrived in the 1920s. Local businesses certainly milk the name; lots of businesses and professionals located in the area have put "Hollywood" in their names.
The main drag of Hollywood is Sandy Boulevard, a very busy arterial road whose heavy traffic limits the "cafe life" appeal of the area. Sandy is one of those weird diagonal streets (like Foster Road in SE) that runs at 45 degrees to the grid, so it runs NE to SW. The diagonal cuts off some of the blocks and make for some curious little islands with some small buildings crammed onto them. Driving along Sandy can be frustrating through Hollywood, because left turns are not allowed at most intersections.
For a Portland urban neighborhood, Hollywood is very car-oriented; perhaps that's because several busy roads intersect in the heart of Hollywood: Sandy Blvd, NE 39th Avenue, and NE Broadway all intersect there, near on-ramps to Interstate 84! The cars have to go somewhere! At some point the retail district in Hollywood seems to have been heavily modified to accommodate the cars; unusual for a Portland urban neighborhood, many Hollywood businesses have small parking lots, in addition to street parking. This is very different than you would find in, say, NW Portland or Hawthorne, where you're largely limited to street parking.
Despite the cars, Hollywood does have decent bus and train service via the Hollywood Transit Center. MAX Red and Blue lines (and starting in the fall of 2009, the Green line) serve the Hollywood TC as do several frequent bus lines taking you north/south on 39th Avenue and elsewhere.
Sandy has an eclectic mix of businesses: some interesting local icons for sure such as the historic Hollywood Theatre (run by a non-profit, it now shows largely art house films) and a few bars and cafes. Yet there are also plenty chain restaurants in the area - a McDonald's, a Subway, etc. A Rite Aid drug store right on Sandy was the site of Portland's original Fred Meyer store. Yet there is a nice Trader Joe's and (coming in summer 2009) a new Whole Foods. There's also a fairly new 24 Hour Fitness gym very close to the Hollywood Transit Center.
Look on a map to see how Sandy Blvd splits the area. North of Sandy, a few blocks from the retail district, you'll find a nice neighborhood area with beautiful homes, a "classic" Portland neighborhood. South of Sandy, there's a wedge between Sandy and I-84, and that area is much less nice. That's where the apartment buildings in the area tend to be. On the south side of I-84 is the very nice Laurelhurst neighborhood (walkable via a pedestrian/bike bridge over the highway from Hollywood Transit Center).
Grant High School, a great high school, is just to the NW of the Hollywood District; if you care about schools, check to make sure your home would be in that district. Hollywood also has a nice public library branch.
The annual Rose Festival Junior Parade (a children's parade) takes place in the Hollywood District, in June.
Hollywood is fairly close to the Portland International Airport, if by chance you will work there or need to fly often. In fact, you can get to PDX quickly via Sandy Blvd to 82nd Avenue without using I-84 - or take the MAX train from Hollywood TC.
Hollywood Theatre, Sandy Blvd, Hollywood District
Hollywood Burger Bar
Neighborhood north of Hollywood retail district
Example of homes, north of retail district
Pictures are all copyrighted by Andrew Hall and may not be used or copied without permission.