For two-columns documents, a semi-manual solution is possible using the wrapfig package. It avoids cluttering the code with ad-hoc material as in Werner’s or Yiannis’ solutions.
\documentclass{article}\usepackage{multicol}% for multiple columns\usepackage{wrapfig}\usepackage{calc}% for computations\begin{document}\pagestyle{empty}\begin{multicols}{2}Wikipedia is a multilingual, Web-based, free-content encyclopedia project. The name is a portmanteau of the words wiki and encyclopedia. Wikipedia is written collaboratively by volunteers, allowing most of its articles to be edited by almost anyone with access to the Web site. Its main servers are in Tampa, Florida, with additional servers in Amsterdam and Seoul.Wikipedia was launched as an English language project on January 15,\begin{wrapfigure}[7]{r}[.5\width+.5\columnsep]{5cm}\itshape``Imagine a world in which every single person on the planet is given free access to the sum of all human knowledge. That's what we're doing''\end{wrapfigure}2001, as a complement to the expert-written and now defunct Nupedia, and is now operated by the non-profit Wikimedia Foundation. It was created by Larry Sanger and Jimmy Wales; Sanger resigned from both Nupedia and Wikipedia on March 1, 2002. Wales has described Wikipedia as ``Imagine a world in which every single person on the planet is given free access to the sum of all human knowledge. That's what we're doing''.Wikipedia has more than six million articles in many languages, including more than 1.5 million articles in the English-language version and more than half a million in the German-language version. There are 250 language editions of Wikipedia, and 19 of them have more than 50,000 articles. The German-language edition has been distributed on DVD-ROM, and there have been proposals for an English DVD or print edition. Since its inception, Wikipedia has steadily risen in popularity, and has spawned several sister projects. According to Alexa, Wikipedia ranks among the top fifteen most visited sites, and many of its pages have been mirrored or forked by other sites, such as Answers.com.There has been controversy over Wikipedia's reliability and accuracy,\begin{wrapfigure}[7]{l}[.5\width+.5\columnsep]{5cm}\end{wrapfigure}with the site receiving criticism for its susceptibility to vandalism, uneven quality and inconsistency, systemic bias, and preference for consensus or popularity over credentials. Information is sometimes unconfirmed and questionable, lacking the proper sources that, in the eyes of most ``Wikipedians'' (as Wikipedia's contributors call themselves), are necessary for an article to be considered ``high quality''. However, a 2005 comparison performed by the science journal Nature of sections of Wikipedia and the Encyclop\ae dia Britannica found that the two were close in terms of the accuracy of their articles on the natural sciences. This study was challenged by Encyclopædia Britannica, Inc., who described it as ``fatally flawed''.\end{multicols}\end{document}The syntax of {wrapfigure} is
\begin{wrapfigure}[number of lines]{alignment}[overhang]{width}...\end{wrapfigure}The whole process of manually positioning the two {wrapfigures} is well explained in multiple-span.txt:
Cutouts in Matching Columns~~~~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~X ~~~~~~~~~~~~~~~~~Y~~~~~~~~~ ~~~~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~Initially, write the document without the wrapfigure, and locate thedesired natural linebreak at "X". (This first step is used for allmethods described here.) Then change to~~~~~~~~X\begin{wrapfigure}[6]{r}[.5\width+.5\columnsep]{6cm}...\end{wrapfigure}~~~~....and run LaTeX again. This will print the figure overlapping the rightcolumn, but no matter. Use this run to locate position "Y" in the text.For the final run, switch to: ~~~~~~~~X\begin{wrapfigure}[6]{r}[.5\width+.5\columnsep]{6cm}...\end{wrapfigure}~~~~.......~~~~~~~Y\begin{wrapfigure}[6]{l}[.5\width+.5\columnsep]{6cm}\vfill\end{wrapfigure}~~~~~~~~~~~Compared to this example, I only adjusted the parameters : 5cm instead of 6cm for the width and 7 lines instead of 6 lines.